Michael Chang - STR Like the Best - Worth it?

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Michael Chang - STR Like the Best - Worth it?

Member since 2026 · 8 posts · 10 votes

Hello all -

I am getting ready to delve into the world of STR to help offset some taxes and generate monthly income. I am an attorney by trade but unfamiliar with real estate. I came across Michael Chang's podcast and his company, STR Like the Best. I have spoken with the company and like what I hear. Those with experience seem like he is legit. Can anyone who has been through his program comment on whether it is worth the financial investment? (Remember you're talking to complete real estate novices here). Would love to hear all positive and negative feedback.

My greatest concern holding me back is whether the unit will pay for itself. I am not interested in carrying two mortgages...Seems like this program will help me identify the right property and put the pieces in place to make it profitable.

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John UnderwoodPro Member

Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes

7mo

I would not pay for a course where the information is readily available for free.

Tons of info on here.

Avery Karl's books are very good.

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Jeff Roth
Real Estate Consultant · Ann Arbor, MI · Member since 2022 · 466 posts · 256 votes
7mo
Hi Michael-
Great question. You are an attorney looking to invest in short-term rentals to offset you income taxes by accelerating the depreciation with bonus depreciation and a cost segregation study after "materially participating" with enough hours for the year to show you qualify to take the active income deduction.
We help investors do that from around the country in Michigan. We partner with a statewide short-term rental management company that has properties nearby to give us on the ground performance data to compare with the STR performance data online. They also offer a menu of services to allow you to pick the things you would like them to do and what you would like to do to get your participation hours.
Recommend Semi-Retired MD for the training. Their next class sign up ends tonight and it's not just for doctors. Check them out.
To Your Success!
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John UnderwoodPro Member
Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
7mo
I would not pay for a course where the information is readily available for free.
Tons of info on here.
Avery Karl's books are very good.
7 Reply
- Russell Cate
  OP
  Member since 2026 · 8 posts · 10 votes
  7mo
  Quote from @John Underwood:
  
  I would not pay for a course where the information is readily available for free.
  Tons of info on here.
  Avery Karl's books are very good.
  
  Thanks @John Underwood. I’ll take a look at her books.
  Time is a premium for me since it’s the only commodity I have to sell as an attorney. Balancing that with kids travel sports etc…taking the time to learn this like I normally would is not a real option unfortunately. I need to fast track it. That’s my thought process.
  1 Reply
- John UnderwoodPro Member
  Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
  7mo
  Quote from @Russell Cate:
  
  Quote from @John Underwood:
  
  I would not pay for a course where the information is readily available for free.
  Tons of info on here.
  Avery Karl's books are very good.
  
  Thanks @John Underwood. I’ll take a look at her books.
  Time is a premium for me since it’s the only commodity I have to sell as an attorney. Balancing that with kids travel sports etc…taking the time to learn this like I normally would is not a real option unfortunately. I need to fast track it. That’s my thought process.
  
  Any questions you have, ask them here. You will get plenty of help for free.
  1 Reply
- Mike Kirby
  Rental Property Investor · New Braunfels, TX · Member since 2021 · 289 posts · 256 votes
  7mo
  Quote from @Russell Cate:
  
  Quote from @John Underwood:
  
  I would not pay for a course where the information is readily available for free.
  Tons of info on here.
  Avery Karl's books are very good.
  
  Thanks @John Underwood. I’ll take a look at her books.
  Time is a premium for me since it’s the only commodity I have to sell as an attorney. Balancing that with kids travel sports etc…taking the time to learn this like I normally would is not a real option unfortunately. I need to fast track it. That’s my thought process.
  
  I agree with @John Underwood, why pay when it's all out there for free. The STR craze that happened 6 years ago is not the same as today. Lots of STR horror stories going on today. Still lots of people trying to sell the dream too. Protect yourself and proceed cautiously.
  
  3 Reply
Mike GrudzienPro Member
Lender · Eugene, OR · Member since 2019 · 2k+ posts · 1k+ votes
7mo
Network locally, find a local investors group, find a REIA. You will both learn and find mentors and partners.
0 Reply
- John UnderwoodPro Member
  Investor · Greer, SC · Member since 2014 · 13k+ posts · 17k+ votes
  7mo
  Quote from @Mike Grudzien:
  
  Network locally, find a local investors group, find a REIA. You will both learn and find mentors and partners.
  A local REIA is a great idea!
  1 Reply
Jon Martin
Member since 2022 · 1k+ posts · 1k+ votes
7mo
There are no secrets. . .. Higher bedroom count, good design, location, amenities, kept clean and well managed is 98% of it. If you are willing to put in the time and money to make it stand out then you can be near the top of almost any market.
2 Reply
- Christopher Tile
  Accountant · Long Island, NY · Member since 2021 · 184 posts · 148 votes
  7mo
  Quote from @Jon Martin:
  
  There are no secrets. . .. Higher bedroom count, good design, location, amenities, kept clean and well managed is 98% of it. If you are willing to put in the time and money to make it stand out then you can be near the top of almost any market.
  
  Love this reply.
  Even in saturated markets, those items (higher bedroom count, good design, location, amenities, kept clean) are most of the battle.
  Often clients will pick a saturated market, and wind up selling their underperforming STRs just a couple years later. In most cases, it's clear why.
  Not that I'd recommend a VERY saturated market to everyone, but there's potential to be a top performer everywhere.
  
  4 Reply
Michael BaumPro Member
Olympia, WA · Member since 2016 · 8k+ posts · 7k+ votes
7mo
Hey @Russell Cate, I am with @John Underwood on this.
There is so much info here that you can peruse and then ask more detailed questions, you don't need to waste cashola (that can be used to get your first STR) on a class or system or whatever.
Just come here and ask!
2 Reply
Andrew SteffensBusiness Member
Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
7mo
I recommend using the forums here as pretty much everything has been asked and answered here already. Next, hire an STR specialist agent in your chose market(s). They already know where it is legal and profitable and that saves you a lot of time. I represent dozens of people currently in the Tampa market who are high income earners doing exactly what you are doing with the accelerated depreciation and they are not spending too much time researching, rather relying on me.
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Nicholas L.Pro Member
Flipper/Rehabber · Pittsburgh · Member since 2018 · 6k+ posts · 5k+ votes
7mo
@Russell Cate

hello, and welcome. i don't invest in STRs, but i follow the market somewhat, because i stay in them, and it's also something i'm interested in.

with that caveat, you mentioned two things that caught my attention - the first reason you listed to invest is for tax purposes, not because you are passionate about hospitality; and then you said you don't really have time to be hands-on. if that's the case... not sure STRs are a good fit for you.

maybe the heavyweights like @John Underwood and @Michael Baum can chime back in with their perspectives but with the market the way it is, and prices and rates high, it's a tough time to want to buy any old property and have it operate itself.
hope this helps you think through things
3 Reply
Russell Cate
OP
Member since 2026 · 8 posts · 10 votes
7mo
Thanks @Nicholas L. My spouse would be largely responsible for the property.
1 Reply
Paras D.
Member since 2021 · 3 posts · 0 votes
7mo
@Russell Cate I have seen the overview of Michael's program when he launched this program and unless it has evolved his experience was with rental arbitrage as opposed to buy and hold. If one of your goals is tax savings I don't believe rental arbitrage would be a good fit.

As folks have said there is a whole lot of info out there but the fear of making a mistake when you have not done STRs before is also real.

BP has once or twice a year Bootcamp as and STR is one of the bootcamps that is not super expensive and is taught by Avery Carl referenced above.

Good Luck with your investment journey always happy to help
0 Reply
- Russell Cate
  OP
  Member since 2026 · 8 posts · 10 votes
  7mo
  @Paras D. Thank you for this insight. My biggest fear is buying the wrong property that doesn't cash flow, I end up dumping my own money into the deal or have to sell at a loss to get out from under things. That has ny decision making paralyzed
  0 Reply
- Christopher Tile
  Accountant · Long Island, NY · Member since 2021 · 184 posts · 148 votes
  7mo
  Quote from @Russell Cate:
  
  @Paras D. Thank you for this insight. My biggest fear is buying the wrong property that doesn't cash flow, I end up dumping my own money into the deal or have to sell at a loss to get out from under things. That has ny decision making paralyzed
  
  The first step is to educate. Start by reaching out to realtors in areas you are interested in. The questions will mount from there. You'll find the property types/areas that provide good returns.
  One step forward will snowball. Nothing is ever as bad as it seems. Allow the connections you build to aid in the decision-making process. This is not something you need to do by yourself, the free education is out there (within the forum or with people on the forum)
  0 Reply
- Dan H.Pro Member
  Investor · Poway, CA · Member since 2015 · 7k+ posts · 8k+ votes
  7mo
  Quote from @Russell Cate:
  
  @Paras D. Thank you for this insight. My biggest fear is buying the wrong property that doesn't cash flow, I end up dumping my own money into the deal or have to sell at a loss to get out from under things. That has ny decision making paralyzed
  I question if you understand the STR tax benefit against W2 income.
  1) the STR must show a taxable loss. With accelerated depreciation, I can see the tax loss in the near term being greater than the actual cost. Note this would be fairly short lived as the accelerated depreciation moves the depreciation forward meaning there is less to depreciate after a certain timespan. If, however, you are experiencing a tax loss with standard depreciation, I question if you in fact are not losing money running the STR.
  2) you must spend more hours than anyone else on the STR. This likely implies no PM or co-host. It may require rotating cleaners.
  
  >I am getting ready to delve into the world of STR to help offset some taxes and generate monthly income.
  
  the tax savings occur only if you show a taxable loss on the STR which mostly implies that it is not generating monthly income (possible exception in short term if combined with accelerated depreciation).
  
  good luck
  1 Reply
- Russell Cate
  OP
  Member since 2026 · 8 posts · 10 votes
  7mo
  Quote from @Christopher Tile:
  
  Quote from @Russell Cate:
  
  @Paras D. Thank you for this insight. My biggest fear is buying the wrong property that doesn't cash flow, I end up dumping my own money into the deal or have to sell at a loss to get out from under things. That has ny decision making paralyzed
  
  The first step is to educate. Start by reaching out to realtors in areas you are interested in. The questions will mount from there. You'll find the property types/areas that provide good returns.
  One step forward will snowball. Nothing is ever as bad as it seems. Allow the connections you build to aid in the decision-making process. This is not something you need to do by yourself, the free education is out there (within the forum or with people on the forum)
  
  Thanks @Christopher Tile this is some of the best advice I've read.
  0 Reply
- Christopher Tile
  Accountant · Long Island, NY · Member since 2021 · 184 posts · 148 votes
  7mo
  Quote from @Russell Cate:
  
  Quote from @Christopher Tile:
  
  Quote from @Russell Cate:
  
  @Paras D. Thank you for this insight. My biggest fear is buying the wrong property that doesn't cash flow, I end up dumping my own money into the deal or have to sell at a loss to get out from under things. That has ny decision making paralyzed
  
  The first step is to educate. Start by reaching out to realtors in areas you are interested in. The questions will mount from there. You'll find the property types/areas that provide good returns.
  One step forward will snowball. Nothing is ever as bad as it seems. Allow the connections you build to aid in the decision-making process. This is not something you need to do by yourself, the free education is out there (within the forum or with people on the forum)
  
  Thanks @Christopher Tile this is some of the best advice I've read.
  
  Love to hear that. Best of luck to you!
  0 Reply
Russell Cate
OP
Member since 2026 · 8 posts · 10 votes
7mo
Thanks for the insight @Dan H. The idea would be for my spouse to be responsible for running the property. We would take bonus depreciation on the property at the outset to help offset my taxes. The way I understand things is that I can take bonus depreciation and have a cost-set study performed on items that can be depreciated over time.
1 Reply
- Dan H.Pro Member
  Investor · Poway, CA · Member since 2015 · 7k+ posts · 8k+ votes
  7mo
  Quote from @Russell Cate:
  
  Thanks for the insight @Dan H. The idea would be for my spouse to be responsible for running the property. We would take bonus depreciation on the property at the outset to help offset my taxes. The way I understand things is that I can take bonus depreciation and have a cost-set study performed on items that can be depreciated over time.
  
  Everything you stated is true but
  1) that moves the depreciation forward. Starting at some point such as year 6 (it will vary per cost seg study) your depreciation basis is lower than standard depreciation. What is the plan for when the forwarded depreciation no longer show a loss? Do you plan to purchase an STR every 5 years?
  2) to offset the taxes, the STR must show a loss. I want my STRs to show a profit (and they do).
  3) STR management is a fair amount of work and has a learning curve. To be good at it takes understanding. My view is the self managed can exceed the average area PM OTA but they will need to learn a lot and work it to do so. This is easiest if it is a passion of the host. I have a friend with a single STR who is crushing it on occupancy (her unit cost enough that her finances on it are marginal) because she is a people person and one of the more empathetic people I have ever met. She enjoys being a host. I have been a STR LL a long time (2 of my units started in 1999) and have a few horror stories (including a fair amount of damage to a spa from this past weekend but guest has already submitted payment) and do not have the passion to self managed. So I have a great co-host that deals with the guests, OTAs, pricing, helps with the permitting (every other year), cleaners, etc. Basically we share handyman because my handyman crew is better than her crew (we self managed our LTRs with a handful of handy people who we are their largest source of work) and managing her (look at monthly statements, discuss any issues (normally the wife as me and co-host are like oil and water), etc. My point is if your wife does not have a passion to co-host, it will be reflected in the ADR but more importantly she will not want the job long as co-host/pm compensation is not high. My time is valuable. If I wanted a job as a co-host or STR manager, I would have that job.
  4) when you sell, the depreciation is typically recaptured.
  
  in summary the STR benefit to offset active income is not beneficial enough by itself that I would suggest purchasing STRs with that being the goal. IMO you are better off purchasing a profitable STR that does not have losses to offset active income. Ideally one that is profitable including co-host/PM compensation otherwise if you self manage you are working for below market rate compensation.
  
  good luck
  
  2 Reply
- Nicholas Fisher
  Los Angeles, CA · Member since 2011 · 1 post · 0 votes
  5mo
  Quote from @Russell Cate:
  
  Thanks for the insight @Dan H. The idea would be for my spouse to be responsible for running the property. We would take bonus depreciation on the property at the outset to help offset my taxes. The way I understand things is that I can take bonus depreciation and have a cost-set study performed on items that can be depreciated over time.
  
  Russell, I'm curious. What did you decide to do? I'm in a similar boat and doing my research. I'm supposed to have a call with Michael's team tomorrow and trying to figure out the best path forward for my situation.
  0 Reply
- Jay HinrichsBusiness Member
  Real Estate Consultant · Summerlin, NV · Member since 2014 · 45k+ posts · 66k+ votes
  3mo
  Quote from @Russell Cate:
  
  Thanks for the insight @Dan H. The idea would be for my spouse to be responsible for running the property. We would take bonus depreciation on the property at the outset to help offset my taxes. The way I understand things is that I can take bonus depreciation and have a cost-set study performed on items that can be depreciated over time.
  
  STR are a lot of work if bonus depreciation is what your after.. look for a nnn investment were you get real bonus depreciation.. I did this with a doctors office and it worked well and its truly passive .. I tried STR and its a ton of work to do on your own.. unless your going to scale it or you really like to be an in keeper.
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  1 Reply
Ashish AcharyaBusiness Member
CPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
5mo
Hey Russell! You’re starting off strong by asking this question here, and you’ve already gotten some really solid responses. I agree with what others have said already. Mike, John, and Jon gave you good direction. Network locally, join some Facebook groups, run the numbers, and keep asking questions as you go.

I see you’re already thinking about the tax side of things, too, which is a great sign. If you really want to get serious about this, I’d start by speaking with a lender so you can run some realistic numbers on your financing options. Then I’d connect with a real estate agent in your target market who works with investors (there are plenty in here you could likely connect with). And then the next step (or maybe even the first step, since you're already considering strategy) is to get with a CPA who understands real estate investing so you can actually build this into a longer-term tax and investment plan, not just a one-off purchase. There are plenty on here. I would choose a few to interview and see which one you connect with.

From a tax standpoint, I think you already understand the real opportunity with short-term rentals (STRs) and that it isn’t just the cash flow, it’s how the activity is classified. If the average stay is short enough and you materially participate in the activity (things like managing bookings, coordinating cleaners, handling guest communication), the IRS may treat it more like an active business rather than a passive rental. In some cases, that can allow you to use strategies like accelerated depreciation (often through a cost segregation study) to generate paper losses that may offset other income, depending on your situation. That’s usually what people are referring to when they say STRs can create tax advantages.

Since you mentioned your spouse would be running it, long-term rentals combined with Real Estate Professional Status (REPS) might also be something to look into, but the requirements are pretty strict, you generally need significant time spent in real estate activities and more than just one property for it to really work.

Overall, you’re thinking about the right things early, just make sure you’ve got the right team around you so you can execute it confidently. There are definitely a lot more people doing it now, but people are still jumping in! Good luck and happy to connect!
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Abhishek SinhaPro Member
New to Real Estate · Northern New Jersey · Member since 2022 · 5 posts · 0 votes
3mo
Hi Russell,
Did you join the STR like the best program for STR. Wondering what decision you made based on the feedback. I am considering the program and would love to hear from you.
0 Reply
Angela Venger
Member since 2026 · 47 posts · 21 votes
3mo
I agree to a point that you shouldn't pay money to a course, IF you have all the tme in the world. You can learn this whole game for free.
Read the books. Listen to every podcast. Come to forums like this one and read every post about STR, every host's mistakes, every lesson learned the hard way. It's all documented somewhere by someone who already paid for it in stress and lost money. Your job is just time and digging.

But if you want learn fast? Money buys speed.

You're an attorney, no real estate background, one mortgage you can't afford sitting empty. That's not the spot to learn by trial and error. Every mistake you make while you're still figuring it out costs real dollars, not just time.
1 Reply
Vijay FriedmanBusiness Member
Miami, FL · Member since 2026 · 766 posts · 122 votes
3mo
Quote from @Russell Cate:

Hello all -
I am getting ready to delve into the world of STR to help offset some taxes and generate monthly income. I am an attorney by trade but unfamiliar with real estate. I came across Michael Chang's podcast and his company, STR Like the Best. I have spoken with the company and like what I hear. Those with experience seem like he is legit. Can anyone who has been through his program comment on whether it is worth the financial investment? (Remember you're talking to complete real estate novices here). Would love to hear all positive and negative feedback.
My greatest concern holding me back is whether the unit will pay for itself. I am not interested in carrying two mortgages...Seems like this program will help me identify the right property and put the pieces in place to make it profitable.

@Russell Cate
That's a smart concern to have. I'd spend just as much time validating the property's projected income and expenses as evaluating any education program. A good STR purchase should still make sense based on the numbers, regardless of whose system you follow.
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Brittney McIntire
Lender · Los Angeles, CA · Member since 2022 · 36 posts · 15 votes
3mo
Hi Russell. I am not sure how much his program charges however, I personally did a mentorship before I dove into my short term rental. Of course all you need to know is online and available for you to learn for free however, for me I work better when I have accountability and a schedule. Being in a mentorship personally helped me a lot. My mentorship helped me with everything from analyzing properties to setting up my property management software to providing lists for what I should have my cleaners do, my photographer do, etc. I know this can all be easily done on your own but the time it saved me was well worth it. I did not have to go searching for all this on my own it was all handed to me. I did do this before AI was really a thing so maybe with AI it would be a lot easier to research but having a whole community to rely on is great. Totally subjective but I was happy I did my mentorship.
0 Reply
- Abhishek SinhaPro Member
  New to Real Estate · Northern New Jersey · Member since 2022 · 5 posts · 0 votes
  3mo
  @Brittney McIntire Do you mind sharing which mentorship program you attended? TIA
  0 Reply
Robin SimonBusiness Member
Lender · Austin, TX · Member since 2022 · 5k+ posts · 4k+ votes
3mo
I have heard its a solid program - as someone who bought my first three Short Term Rentals last year and executed the cost seg / active management strategy there is a lot to worry about and learn, so it is very helpful to have guidance beyond just scattered research
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Brittney McIntire
Lender · Los Angeles, CA · Member since 2022 · 36 posts · 15 votes
3mo
@Abhishek Sinha Of course! I did the one with Madeleine Raiford-Holland. If you search her you can view the program info on her site
0 Reply
- Abhishek SinhaPro Member
  New to Real Estate · Northern New Jersey · Member since 2022 · 5 posts · 0 votes
  3mo
  @Brittney McIntire thanks for your guidance. Sure, will do.
  0 Reply

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