STR Like The Best

Michael Chang
  • 5.0 (69)
  • Entrepreneurship
  • Updated Weekly

Proven strategies and insights from successful STR investors and wealth-building experts. We share methods that help high-income earners protect their income, build lasting wealth, and compound their finances for the long term.

  1. 2d ago

    100% Bonus Depreciation Is Back Permanently (And Most High-Income Professionals Still Don't Know It)

    For years, high-income professionals watched the STR tax loophole phase out and assumed it was gone for good. It's not. And the window to act is open right now. In this episode, I sit down with Ryan Bakke, CPA and founder of Tax Strategy 365, to break down everything you need to know about the return of 100% bonus depreciation, how to use it correctly, and how to make sure you never have to sweat an IRS audit. Ryan left Deloitte to build one of the most successful CPA firms in the country, now approaching eight figures in revenue with 60 employees. He has helped hundreds of high-income professionals use the STR tax loophole to legally offset their W2 income and build real, lasting wealth outside of their careers. If you are a doctor, surgeon, or high-income professional wondering whether this strategy is still valid and whether it is right for you, this episode is required listening. We break down: Why 100% bonus depreciation is now permanent under the One Big Beautiful Bill, and what that means for short-term rental investors going forward The exact tax code carve-out (Section 469) that makes the STR loophole legal, and why less than 300 characters in the tax code changed everything Why holding your STR long-term is not optional, and what depreciation recapture will cost you if you sell too soon The biggest documentation mistakes investors make that get them destroyed in an audit, and the log strategy that protects you What the IRS actually asks in an audit interview and why your story matters as much as your numbers Why the 30-year fixed mortgage is the single greatest wealth-building tool available to Americans, and why most high-income professionals are ignoring it The bottom line: The strategy is legal, it is permanent, and the investors who understand it are building generational wealth while their peers are handing half their income to the government. LEARN MY STR INVESTING & STRATEGIES 🔥  https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    32 min

  2. 2d ago

    REPS vs. the STR Tax Loophole: The $25,000 Mistake We Made (And How to Avoid It)

    Most W2 earners think REPS and the STR tax loophole are the same thing. They are not, and confusing the two could be costing you tens of thousands of dollars a year. In this episode, Michael and Liz break down the real difference between real estate professional status and the STR tax loophole, why one is nearly impossible for full-time employees, and how the 100-hour rule opens the door for W2 couples who want to build wealth without quitting their jobs. We break down: The core difference between REPS and the STR tax loophole, and why one does not lead to the other Why getting your real estate license does not qualify you for REPS (and the misconception that trips up almost everyone) The 750-hour requirement for REPS and why it is virtually impossible if you hold a full-time job The three requirements to qualify for the STR tax loophole, including the 7-day rule and material participation The $25,000 tax mistake we made with the wrong CPA, and how to find a thought partner instead of just a tax filer Why stay-at-home parents are uniquely positioned to satisfy the 100-hour rule and help their family build generational wealth The bottom line: you do not need 750 hours, a real estate license, or a $1,000-an-hour tax lawyer. You need the right strategy, 100 hours, and personal ownership of your financial future. LEARN MY STR INVESTING & STRATEGIES 🔥  https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    14 min

  3. Jun 19

    There Is No Perfect Time to Buy (And Why Waiting Is the Most Expensive Mistake STR Investors Make)

    You've done the research. You've looked at the markets. You've run the numbers. So why haven't you bought yet? In this episode, Michael and Liz break down the most common trap STR investors fall into: waiting for the perfect moment that never comes, and the real cost of staying on the sidelines. We cover a lot of ground here, from how to train your eye to spot an outlier property, to the mindset shift that separates investors who build wealth from those who stay stuck in the research loop. We break down: The "buy yesterday" principle and why real estate rewards action over timing How analysis paralysis keeps smart, high-income professionals from ever pulling the trigger What to actually look for in a property, and how Michael spotted a misrepresented A-frame in the Catskills that no one else saw coming The pros and cons of buying at different points in the year, and why the "wait until Q4" strategy backfires more often than not Why the STR strategy is a real estate investment strategy first, and a tax strategy second, and what happens if you get that backwards Why bonus depreciation being permanent in 2025 makes getting the first one right more important than ever The bottom line: there is no perfect time, but the investors who do the work now are the ones who move fast when the right deal appears. LEARN MY STR INVESTING & STRATEGIES 🔥  https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    17 min

  4. Jun 12

    The Real Cost of Doing Your STR Journey Alone (And the 4 Phases Where Most Investors Get It Wrong)

    Most high-income professionals think they can figure out short-term rental investing on their own. The cost of that assumption is higher than you think. In this episode, I sit down with Liz to break down the real price of doing it alone across every phase of the STR investment journey, from finding the right market all the way to managing revenue once you go live. We have been running short-term rentals since 2016, built a portfolio of 30+ properties generating $2.3M a year, and made every one of these mistakes ourselves before we figured it out. This episode is the honest conversation we wish someone had with us earlier. We break down: Why high-income professionals get stuck in analysis paralysis during the search phase, and why looking at multiple markets at once is the fastest way to end up nowhere The turnkey trap: why a property making $100K on a $1M purchase can still be losing you money if you don't know how to read the full expense picture What happens when you go to a big bank instead of an STR-specific lender, including the week Chase told us we needed 25% down instead of 20% at the last minute Why DIY design costs you more than hiring a professional, and how doing it yourself can delay your launch by 2 to 4 weeks and cost you a full month of mortgage payments The revenue management mistake we made for our first 2 years, why tools like PriceLabs and Beyond are not a strategy, and how we finally fixed it by hiring someone full-time Why the biggest hidden cost in this whole journey is not money. It is time, decision fatigue, and the price of not listening to the right people The bottom line: Going it alone does not make you more capable. It just makes the lessons more expensive. LEARN MY STR INVESTING & STRATEGIES 🔥  https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    32 min

  5. May 29

    From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks Like

    From $180K Tax Bill to $110K Refund: What 9 Months in the Program Actually Looks Like Most high-income couples know they're overpaying on taxes. Very few actually do something about it. In this episode, Michael sits down with Ashish and Smita, a Bay Area dentist and finance professional, to walk through their first 9 months in the STR Like The Best program, from their first property in Colorado to filing the most satisfying tax return of their lives. This isn't a highlight reel. It's the real story, including the self-doubt, the market search, the launch, the guests who left the hot tub uncovered, and the moment their CPA told them to expect a very large refund. We break down: How a $180K tax bill during Ashish's nose surgery recovery sent them down a rabbit hole that changed everything Why they chose Colorado over Hawaii, and how the mentorship helped them stop overthinking market selection and just move What their first season actually looked like, covering the mortgage in off-peak months and heading into their best month ever How they got $94K back in federal taxes and $16K from California in their very first year with one property Why "done for you" STR programs legally cannot qualify you for the tax benefits, and what the IRS actually requires The 4 things Ashish and Smita would tell their pre-July 2024 selves if they were still on the fence The bottom line: the STR tax loophole is real, it works, and it works best when you stop waiting for the perfect moment and just do the work. LEARN MY STR INVESTING & STRATEGIES 🔥  https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    48 min

  6. May 22

    The Fear of Out-of-State Investing Is Costing You Six Figures in Tax Savings Every Year

    You live in California. Or New York. Or any other high-cost, high-tax state where buying a short-term rental locally makes zero financial sense. So you do nothing. And every year you wait, you leave six figures in tax savings on the table. In this episode, Michael and Liz break down exactly how they built a 30+ property STR portfolio worth $2.3M in annual revenue while managing everything remotely from New York City, and why out-of-state investing is not only possible, it's the smartest move high-income W2 earners can make right now. This is not a guest episode. This is 25 minutes of hard-won experience from two people who have done it, coached 30-40 California-based clients through it, and figured out every obstacle along the way. We break down: The mindset shift that unlocks everything, because if you believe you can't manage a property 2,000 miles away, you never will, and why that belief is costing you more than you think The exact tech stack for remote management including smart locks, automated guest codes, $30 cameras from Amazon, noise monitors, and smart thermostats that let you run a property entirely from your phone How to hit your 100-hour material participation requirement while investing out of state, including the desktop work, vendor calls, guest communication, and setup coordination that count toward your hours The stay-at-home spouse advantage and why a married couple where one partner stays home is one of the most powerful setups for the STR tax loophole How to document your hours the right way, using smart lock entry codes per cleaner, camera logs, and access records that hold up if the IRS ever comes knocking Why "we'll do everything for you" STR programs are a tax trap, and what actually happens three to four years later when the audit letter arrives and those people are long gone The bottom line: The technology exists, the communities exist, and the strategy works. The only thing standing between you and six figures in annual tax savings is the belief that you have to live near your property to own it. LEARN MY STR INVESTING & STRATEGIES 🔥  https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    26 min

  7. May 15

    From Screwdrivers to Systems: Launching Property #8 (Lessons From Property #1)

    We closed on property #8 last week. And the difference between then and now is not even close. In this episode, I sit down with Liz to walk through what the first week post-closing actually looks like on our eighth Tennessee cabin, and contrast it against the chaos of doing it all ourselves for the very first time back in 2020. This is not theory. This is what we are doing right now, in real time, to hit the 100-hour material participation requirement and get this property launched before July 4th. We break down: Why Liz is logging 4 hours a day remotely and what that work actually looks like, from coordinating electricians for the hot tub and sauna to vetting pest control, bear-proof trash cans, and fire safety vendors How we accumulated 40+ hours in the first week alone, and why that number matters for unlocking the STR tax loophole on our active W-2 income The vendor vetting mistake first-time investors make on Facebook, and why a comment section full of five-star reviews does not mean what you think it does What our Day One plan looks like now versus property #1, when we drove down from New York with a car packed to the gills and a screwdriver we did not know how to use How the material participation hours stack as you scale, and why hitting 100 hours gets easier with every property you add to your portfolio Why we use the STR Tax Loophole app to log and document every hour, so our records are organized, defensible, and ready if the IRS ever comes asking The bottom line: the work does not get smaller as you scale. It gets smarter. And knowing exactly what to do, who to call, and how to log it is what separates investors who get the tax benefit from those who leave it on the table. LEARN MY STR INVESTING & STRATEGIES 🔥  https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    23 min

  8. May 8

    From Shoe Reseller to Real Estate Developer: How Rajan Chida Built Royal Oak Retreats at 23

    Most 23-year-olds are figuring out their first job. Rajan Chida was turning down JP Morgan to build luxury cabins in Virginia. In this episode, I sit down with Rajan Chida, co-founder of Royal Oak Retreats, to talk about how he went from reselling shoes on eBay in college to developing ground-up luxury STR cabins and building a 550K social media following in under a year. Rajan's story is not your typical real estate success story. It's about stacking capital early, betting on yourself at the right moment, and using social media as leverage in a way that most developers with 10 years of experience still don't understand. We break down: How Rajan funded his first real estate project with shoe reselling money he saved from age 17, and why starting a "job" at 17 gave him a head start most investors don't get until their mid-twenties Why his 550K following didn't convert to bookings the way he expected, and the pivot to female travel influencers that finally got Royal Oak Retreats fully booked The permitting nightmare in Warren County, Virginia that nearly derailed the entire project, including a disgruntled neighbor, a six-page complaint full of false claims, and a road he had to build just to get the permit approved How tariffs forced him to resource his signature window walls from Poland, adding three months of delays and zero construction progress Why he turned down his JP Morgan offer two weeks before his start date, and the conversation with his dad that gave him the confidence to make that call The pre-deposit playbook he's using for cabins two and three, including $50 deposits, VIP early access, and how Travis at Outpost X raised $1M before breaking ground The bottom line: social media is not just a marketing tool. In the hands of the right person, it replaces the track record, the connections, and the credibility that used to take a decade to build. LEARN MY STR INVESTING & STRATEGIES 🔥  https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

    43 min
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5
out of 5
69 Ratings

About

Proven strategies and insights from successful STR investors and wealth-building experts. We share methods that help high-income earners protect their income, build lasting wealth, and compound their finances for the long term.

Information

  • Creator
    Michael Chang
  • Years Active
    2023 - 2026
  • Episodes
    94
  • Rating
    Explicit
  • Copyright
    © 2026 STR Like The Best
  • Show Website
    STR Like The Best

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