Rent to retirement STR

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Rent to retirement STR

Ang Sherpa
New to Real Estate · Member since 2026 · 13 posts · 12 votes

Hi,

I am high income W2 earner with stay home spouse with 3 young kids under 10. We have decided to invest in real estate - both STR and LTR. I plan to invest in Allentown and Bethlehem, PA. I would love to connect with anyone investing or working in these areas to form a team. I am looking for duplex or triplex, with cosmetic repair/value add, 200-400k. Feel free to reach out.

I can't seem to find much information on STR unlike LTR. Where should I start for more knowledge on STR? Would love any tips/suggestions regarding STR. Listening to biggerpockets podcast, I came across rent to retirement offering STR? Has anyone used them? What has been your experiences? All and any comments would be very helpful.

Thank you

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Yim Gong
Member since 2014 · 1 post · 1 vote
2w

Hi Ang, you can listen to the Short Term Shop podcasts (with Avery Carl) and STR like the Best (with Michael Chang) podcasts. I find these 2 to be very helpful. I am also new to the STR journey and we are in the process of moving LTRs to STR properties. Best of luck with this.

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  • Kasing Ng
    Accountant · San Francisco, CA · Member since 2026 · 122 posts · 75 votes
    2w

    Hi Ang, I can't help much on the STR learning side, that's not my area. Where I can is the tax piece, since it's a real difference for someone in your spot.

    An STR can beat a long-term rental on taxes: if your average guest stay is 7 days or less and you materially participate (real, logged hours), the losses can offset your W2 income without needing real estate professional status, which long-term rentals would require. The loss usually comes from front-loading depreciation with a cost segregation study. Worth running past a CPA before you structure it.

    0Reply
    • Terry ConwayPro Member
      Member since 2024 · 4 posts · 1 vote
      1w

      Hi Kasing, Isn’t a CSS costly for one property?

      0Reply
  • Trent Reeve
    Atlanta · Member since 2022 · 718 posts · 648 votes
    2w

    Ang, i do not mean to come across mean. But if you cant find information on STR's, you arent looking very hard. This forum alone has great information on STR's. Plenty of Facebook groups as well that are a wealth of information.

    0Reply
    • Trent Reeve
      Atlanta · Member since 2022 · 718 posts · 648 votes
      2w

      if you cant find any FB groups, i would be happy to share some of the ones I am in

      0Reply
    • Ang Sherpa
      OP
      New to Real Estate · Member since 2026 · 13 posts · 12 votes
      2w

      I been binging podcast because it works best for me so I bet I am missing on the knowledge from forum. I gotta start reading more forums now for STR. Also, I learn from reading books. Any good STR book recommendations? Thank you.

      1Reply
    • Terry ConwayPro Member
      Member since 2024 · 4 posts · 1 vote
      1w

      @Trent Reeve Would it be okay to share those groups here? If not, please DM me as I would like to join them.

      0Reply
  • Amit PatelBusiness Member
    Property Manager · Bartlett, IL · Member since 2025 · 183 posts · 71 votes
    2w

    Welcome! We’re long-term rental folks in the Chicago suburbs, so I can’t speak to Rent to Retirement or Allentown directly, but a few things I’d tell any new investor:

    • Check the rules first. STR regulations change city by city and even by zone. Confirm with Allentown and Bethlehem what's allowed and what licensing is required before you fall in love with a property.

    • STR is a hospitality business, not just a rental. Cleaning, guest messages, furnishing, and seasonality add up. With 3 young kids, be honest about how much time you have, or budget for a manager.

    • With any turnkey provider, ask for real numbers. Actual 12-month operating history on properties they manage, not projections. Then check the comps yourself on AirDNA or similar.

    • Talk to a CPA early. The STR tax strategy many W2 earners hear about depends on material participation rules, and the details matter.

    • Consider mid-term rentals. The Lehigh Valley has big hospital systems, and travel nurses can be a nice middle ground between STR income and LTR stability.

    A duplex where one side is LTR and the other is STR or mid-term is a great way to learn both without betting everything on one.

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    • Ang Sherpa
      OP
      New to Real Estate · Member since 2026 · 13 posts · 12 votes
      2w

      Thank you. This is very helpful, especially the part about mid term rental and duplex with o e STR and LTR. I definitely have more homework to do.

      0Reply
  • Yim Gong
    Member since 2014 · 1 post · 1 vote
    2w

    Hi Ang, you can listen to the Short Term Shop podcasts (with Avery Carl) and STR like the Best (with Michael Chang) podcasts. I find these 2 to be very helpful. I am also new to the STR journey and we are in the process of moving LTRs to STR properties. Best of luck with this.

    1Reply
    • Marc MoraPro Member
      Investor · Fort Lauderdale, FL · Member since 2026 · 203 posts · 28 votes
      4h

      @Yim Gong, moving long-term rentals over to short stays is a big shift, and the numbers can look very different once cleaning and vacancy hit. I'd convert one first and run it for a full season before moving the rest. If a second opinion along the way would help, I'd be open to it. Are you managing the short-term rentals yourselves? What made short-term rentals the strategy you chose?

      0Reply
  • Ashish AcharyaBusiness Member
    CPA, CFP®, PFS · Sarasota, FL · Member since 2017 · 5k+ posts · 3k+ votes
    2w

    Ang, you're getting some good advice here. I'd add one thing: don't choose an STR just because of the potential tax benefit.

    Since you're looking at both STRs and LTRs, I'd actually underwrite the same type of property both ways and compare the numbers side by side. Look at the purchase price, financing, realistic revenue, vacancy, management, cleaning, insurance, taxes, CapEx, and then layer the tax strategy on top.

    The STR rules can create a very different tax picture from a traditional long-term rental, but the actual facts and your level of participation matter. Your spouse's involvement can also be relevant, so I'd document what each of you is actually doing rather than assuming the tax treatment based on the fact that one spouse is home.

    One other thing I'd look at is whether you qualify as a Real Estate Professional (REPS). If you do and meet the material participation requirements, you may not need to choose an STR over an LTR just for the tax benefit. Both can potentially provide nonpassive rental losses when the requirements are met.

    I’d also have the CPA look at the strategy before you close, especially if you’re considering cost segregation. The goal should be to find a property that works financially first and then make the tax strategy as efficient as possible.

    A duplex where one side is LTR and the other is STR or MTR could also be an interesting way to learn both models without putting the entire property into one strategy.

    Feel free to DM me, I’d be happy to send over a few resources that might be helpful.

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  • Nicholas L.Pro Member
    Flipper/Rehabber · Pittsburgh · Member since 2018 · 6k+ posts · 5k+ votes
    2w

    @Ang Sherpa

    i don't invest in STRs, but I'd caution you - all i know is what you wrote from your post, and it sounds like you're pretty busy. so, i'm assuming your spouse is going to do some of the heavy lifting? the only way you're going to make money on an STR is to be a higher performer, and so you need to ask yourself how you're doing to do that. anyone can buy a random property and list it on AirBNB. But that doesn't mean you'll make any money.

    and... the returns on LTRs have gone to zero, so unless you are going to do some kind of value add or niche strategy... there's nothing there.

    hope this helps

    0Reply
  • Aaron ZimmermanBusiness Member
    Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
    2w

    Ang - I would highly recommend the podcast short term rental riches. Has a lot of good tactical information.

    There’s also a podcast by bill faeth that’s quite good too.

    As other CPA’s have said, don’t forget the tax side as there are some real benefits. I would be tracking hours once you’re under contract for the property. I’d map out if you can meet requirements to shift the income from passive to nonpassive and write off against w-2 income.

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  • Andrew SteffensBusiness Member
    Tampa, FL · Member since 2022 · 4k+ posts · 3k+ votes
    2w

    Hey Ang, welcome!

    Although I am native to Southern NJ so I am personally aware of the markets you mentioned, I am not an expert in STR's there. I am now primarily based in Tampa Bay area FL where I broker and manager people's property. I have a lot of clients with a similar profile to yours. I would say more important than teaming up with investors is finding a knowledgable agent specializing in STR in that area. I do happen to know one if you want a referral.

    Best of luck!

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    • Ang Sherpa
      OP
      New to Real Estate · Member since 2026 · 13 posts · 12 votes
      2w

      Hi, Yes I would love to connect with local real estate agent specializing in STR. Thank you.

      0Reply
  • Jason MalabuteBusiness Member
    Accountant · Los Angeles, CA · Member since 2016 · 2k+ posts · 914 votes
    1w

    On the tax side, an STR can work very differently from a long-term rental. If the average guest stay is 7 days or less and you actually materially participate, with real hours you can document, the loss may be treated as nonpassive, which means it could offset your W-2 income without you needing real estate professional status. Many people pair that with a cost segregation study to speed up depreciation, which is usually where the big early loss comes from. I'd keep a simple log of who did what and when, and run the plan past a CPA before you close. The exact answer depends on your facts, so check with your own CPA or tax advisor. Do you and your spouse plan to self-manage the STR or hire a property manager?

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  • Matthew MorrowBusiness Member
    Investor · PA - NY - NJ · Member since 2019 · 959 posts · 345 votes
    1w

    @Ang Sherpa hey, me again. I'm a long-term rental guy, so I'll leave the STR podcasts to the people above who run them. One thing I'd do before you get too far is check each city's rules on short-term rentals and the zoning for the exact property, because that can change from one street to the next. A duplex where you could run one side short-term and the other long-term gives you a fallback if the short-term side doesn't work out. On the turnkey companies, I haven't used them, so I'd ask for owners you can talk to directly. Hope that helps.

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  • Gregory AcsPro Member
    Lender · MD · Member since 2025 · 270 posts · 99 votes
    1w

    For STRs, I'd start by checking local regulations, occupancy trends, and operating costs before comparing returns with long-term rentals. Financing can also look different depending on how you plan to use the property.

    Are you planning to finance your first duplex or triplex, or purchase with cash?

    0Reply
  • Basit SiddiqiBusiness Member
    Accountant · New York, NY · Member since 2015 · 8k+ posts · 3k+ votes
    5d

    I don't think of STR when I think about Allentown or Bethlehem.
    I don't see it often mentioned as an area where people come to visit for a few days or where there are major conventions that come to.

    It still may work as a STR market but I would be skeptical. See what is being offered on airbnb/vrbo and see how often listings are booked.

    I think they are great LTR markets that offer great cash-flow and appreciation potentials.

    Best of luck!

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  • Christopher Tile
    Accountant · Long Island, NY · Member since 2021 · 193 posts · 157 votes
    4h

    There's a lot of good information/episodes from the TaxSmart REI podcast. Scroll through their list of episodes and you'll find various short-term rental-focused podcasts.

    As it relates to team building - I would start by finding an investor-focused realtor in the area that you are pursuing. Most of the time they can actually help fill the gaps in your team, whether it be a handyman, a plumber, an HVAC technician, etc. They likely already have the connections in that area for you through dealing with investors in the past.

    In addition it's fair to note that you'll need a real estate-focused CPA to record these strategies correctly and strategize with you during the year. Meaningful tax savings are unlocked before the year even starts and during the year. When the year closes we are extremely limited in how we can help on the advisory side. 400k of value add can translate to substantial depreciation if tracked/capitalized correctly. Don't wait until tax filing time to start having conversations. You will miss out on 10s of thousands of depreciation if you working with an incompetent CPA.

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