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. 4D AGO

    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

  2. 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

  3. MAY 1

    The Real Foundation of Our STR Business (It Has Nothing to Do With Real Estate)

    Most people think building a successful STR portfolio comes down to markets, numbers, and design. They're missing the one thing that actually makes or breaks everything. In this episode, I sit down with Liz to talk about what has quietly powered every risk we've ever taken, every property we've bought, and every hard moment we've fought through together over the last 10 years. This isn't a real estate tactics episode. It's the one we probably should have recorded sooner. We break down: How Michael's belief in Liz on a subway ride in 2017 led her to quitting her job and going all in on STR Why mutual belief between spouses is a superpower most people completely overlook The moment I lost confidence in myself and what Liz said that brought it back What our "Corona Battle Plan V2" spreadsheet reminded us about working through the hardest seasons together Why cutting your spouse down to keep them close is one of the most poisonous things you can do in a relationship How we divided responsibilities across a 30+ property portfolio so we each lead where we're strongest The bottom line: If you know your spouse has your back no matter what, you will take bigger risks, make better decisions, and build something neither of you could have built alone. 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/

    19 min

  4. APR 24

    The Market Is Uncertain. Your Tax Bill Isn't. Why We're Buying Property Number Eight Now.

    There's always a reason not to buy. In 2020 it was COVID. In 2022 it was rising rates. Today it's tariffs, gas prices, and AI uncertainty. The investors who waited are still waiting. In this episode, I sit down with Liz to walk through exactly why we're closing on our eighth short-term rental, a $2.1M property, despite everything happening in the headlines right now. We're not ignoring the noise. We're explaining how we filter it, why the STR tax loophole makes buying now more compelling than ever, and how being a married couple investing together is one of the most underrated advantages in real estate. We break down: Why there's always a reason not to buy, and why waiting has cost investors more than any recession The exact data process Liz uses to find underserved markets and identify the right property How the 100-hour rule works as a married couple and why your combined hours are more powerful than you think Why we pushed closing back 10 days on this deal and what the due diligence process actually looks like The basis step-up strategy we're using to pass this portfolio to our kids tax-free Why the One Big Beautiful Bill has made STR assets more valuable than they were a year ago The bottom line: uncertainty is permanent. Your tax bill is optional. 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/

    21 min

  5. APR 10

    Why Married Couples Have an Unfair Tax Advantage (And Exactly How We Use It)

    Most married couples filing jointly have no idea they are sitting on one of the most powerful tax advantages in the entire tax code. In this episode, Michael sits down with co-host Liz to break down exactly how married couples can use the 100-hour material participation rule to qualify for the short-term rental tax loophole, and how they are using it right now across 7 properties with a $2.1 million deal currently in contract. This is not a theoretical conversation. This is exactly what Michael and Liz are doing in real time, with two young kids, multiple properties, and a six-figure tax liability on the line. We break down: What the short-term rental tax loophole actually is and how it allows you to offset W2 income, 1099 income, and capital gains with paper losses from depreciation Why married couples can combine their hours and how that means one spouse doing 10 hours and the other doing 10 hours counts as 20 hours from a material participation perspective The exact hours Liz has logged in the last 16 days since going under contract on their $2.1 million Tennessee property, including design work, vendor coordination, and mood board creation What Michael's day one plan looks like and how he is managing insurance, loans, cleaners, and an operational team before they even close on April 16th How the post-close launch phase is the easiest way to knock out your hours and why a week on the ground at your property can get you to 100 hours faster than you think Why 100% bonus depreciation is back as of July 2025 and what that means for high-income couples who are ready to stop paying six figures in taxes every single year The bottom line: being married is not just a life decision. With the right strategy, it is one of the most powerful tax advantages available to working professionals in America today. 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/

    27 min

  6. APR 3

    Why Being a Stay-at-Home Parent Is the Most Underrated Tax Strategy for High-Income Couples

    Why Being a Stay-at-Home Parent Is the Most Underrated Tax Strategy for High-Income Couples Most high-income couples think staying home means giving up financial contribution. They're wrong. In this episode, Michael sits down with co-host Liz to break down why being a stay-at-home parent is one of the most powerful tax strategies available to high-income couples, and how they have used it to save six figures in taxes while building a 30-property portfolio generating $2.3M per year. This is not a conversation about babysitting and diapers. It is about identity, wealth building, and a tax strategy most CPAs never explain correctly. We break down: The 100-hour rule vs. the 750-hour REP requirement and why most people confuse the two, and why that confusion costs them a fortune How one spouse staying home creates the perfect material participation setup for the short-term rental tax loophole, even if the other spouse earns seven figures The identity guilt that stops smart, driven people from walking away from their careers and how STRs let you keep both Why a tax refund is not free money and what to actually look at on your return to understand your real tax burden How to hire your kids into the business to compound family wealth and reduce taxes even further Estate planning as the next frontier for STR investors who are building a legacy, not just a portfolio The bottom line: the stay-at-home parent is not the one sacrificing for the family. With the right strategy, they are the one saving it the most money. 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 www.thestrtaxloophole.com 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/

    22 min

  7. APR 3

    The Real Reason We Know Which STR Markets Work (It's Not What You Think)

    Most investors open AirDNA, look at the numbers, and think they've done their research. They haven't. In this episode, I sit down with my co-host and wife Elizabeth to pull back the curtain on the exact process we use to evaluate STR markets for our clients and ourselves. We've been doing this for 10 years. We've survived the pre-COVID boom, the COVID collapse, and the post-COVID correction. And in that time, we've built a network, a process, and a level of market depth that most investors don't even know exists. We break down: Why AirDNA is a great starting point but will mislead you if you stop there, and how we layer in agent intel, property manager data, and on-the-ground conversations to get the full picture The exact questions Liz asks every broker and property manager before recommending a single market to a client, including regulation landscape, price range fit, and occupancy opportunity Why market selection is the one thing you can't get wrong, and how we've seen first-time investors struggle not because they operated poorly, but because they started in the wrong market How Liz has analyzed close to 200 properties in just the first two months of 2025, and why that repetition is what separates real market knowledge from guesswork The matching process we use to pair high-income clients with the right market for their budget, timeline, and risk tolerance, from $750K inland properties to $1.5M+ beach markets Why the work doesn't stop once you find a property, and what it actually takes to go from closing to a fully optimized, revenue-generating STR The bottom line: anyone can look at data. Very few people know how to read it, layer it, and act on it. That's the difference between guessing and knowing. 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 www.thestrtaxloophole.com 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

  8. MAR 20

    The STR Financing Blueprint: When to Use DSCR Loans, Second Home Loans, and Everything in Between

    Most STR investors hit a wall around property 3 or 4. Not because they run out of deals, but because conventional lenders start stacking paperwork, haircuts, and restrictions that make it nearly impossible to keep moving. In this episode, I sit down with Robin Simon, author of The Book on DSCR Loans, to break down every financing option available to short-term rental investors and exactly when to use each one. Robin spent years inside the DSCR lending industry, took a year off to write a 715-page book on the subject, and used that same time to buy three STRs himself using the strategies he teaches. This is the conversation I wish I had before I started scaling. We break down: What DSCR loans actually are and how they're different from conventional financing, including why they look at the property instead of your W-2 The second home loan trap most new investors fall into, and why the 180-day occupancy rule makes it nearly impossible to cash flow Why the 5 to 50 property range is the sweet spot for DSCR loans, and when conventional financing still makes more sense How DSCR loans work with LLCs, partnerships, and trusts, and why serious investors structure it this way from the start The connection between DSCR loans and the STR tax loophole, and how using both together lets you keep scaling without your tax returns slowing you down What Robin learned buying three STRs himself, including the paperwork reality that conventional lenders put high earners through The bottom line: the financing tool you choose determines how fast you can scale, and most high earners are using the wrong one. 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/

    21 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
    88
  • Rating
    Explicit
  • Copyright
    © 2026 STR Like The Best
  • Show Website
    STR Like The Best

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