Getting started in the STR world
Member since 2026 · 2 posts · 0 votes
Getting started in the STR world
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Rental Property Investor · Lakeland Florida · Member since 2026 · 4 posts · 2 votes
3dCongrats on closing. Two things I'd check before you buy anything else — I own and manage short-term rentals in Florida and manage properties in South Carolina and Georgia, and both of these have cost me time.
The master deed beats the zoning map. A parcel can be zoned for short-term use and still be blocked by the building's declaration or HOA bylaws. Those are a private contract between owners and they're enforceable regardless of what the city permits. I own four units in a building where the city allows nightly rentals and the declaration sets a seven-night minimum — the declaration wins. Get the recorded declaration and current bylaws before you write an offer, not a summary and not what the seller's been doing. A rule nobody enforces today is still a rule.
Check the conversion overlay on anything oceanfront. Myrtle Beach adopted a Short-Term Rental Conversion Overlay in late 2024 that runs opposite to most coastal regulation — in buildings of more than two units between Kings Highway and the ocean, units can't be leased for 90 continuous days or more, and back-to-back shorter leases to work around it are explicitly a violation. If you hold four oceanfront units and the market softens, the long-term fallback may not be there. Confirm the current text with city Planning and Zoning rather than a forum post, mine included.
One suggestion on the four-unit plan: consider buying them in the same building. One cleaner doing consecutive turnovers with no drive time, shared linen inventory, one maintenance trip covering several issues. Four scattered units is roughly four times the work. Four in one building isn't much harder than two. The tradeoff is concentration risk — one HOA decision or one assessment hits everything at once.
Also worth a call to your insurer before the first booking. A standard HO-6 usually isn't written for paying guests.
Happy to answer anything specific.
— Glen
7 Replies
- 6dAshish AcharyaBusiness MemberCPA, CFP®, PFS · FL · Member since 2017 · 5k+ posts · 3k+ votes
Scott, you're already ahead of a lot of first-time STR buyers because you've set up the LLC, banking, business license, and you're actually underwriting before buying.
The biggest thing I’d focus on now is not letting the portfolio goal push you into the first deal too quickly. If you want four STRs over four years, property #1 needs to teach you the systems without putting too much pressure on your cash reserves.
For Myrtle Beach, I'd underwrite the full operating picture: seasonality, realistic occupancy, cleaning, utilities, management, furnishing replacement, insurance, HOA rules, local STR requirements, and how the property performs outside the peak months. I'd also have a backup plan for what happens if STR regulations or demand change.
From the tax side, start tracking things correctly from day one. For a qualifying STR, average guest stay and material participation can matter a lot. If the average stay is seven days or less and you materially participate, losses may potentially be treated as nonpassive, which can make cost segregation much more useful. Our STR materials specifically emphasize average stay, material participation, placed-in-service timing, and documentation.
I’d also keep furnishing and improvement costs broken out instead of lumping everything together. Once the property is placed in service, depreciation starts, and cost segregation may help accelerate deductions depending on the facts.
One last thing: if you eventually move into one of the STRs personally, that can change the tax treatment, so I’d plan the personal-use transition before it happens rather than after.
Feel free to DM me, I'd be happy to send over a few STR tax resources that might help you get the first one set up correctly.
INVESTOR FRIENDLY CPA®5241 Reviews - 5dMyrtle Mike ThompsonBusiness MemberRealtor · Myrtle Beach, SC · Member since 2016 · 350 posts · 204 votes
Hey Scott,
Congrats on the personal vacation condo you just bought here in Myrtle Beach. I hope you and your family get some great use out of it. I'm sure you already have an agent you're working with, but feel free to reach out if you'd like any guidance or suggestions on the STR. I can help fact check Claude and Rabbu, recommend areas/projects to avoid, etc.
Myrtle Mike Real Estate580 Reviews - Rental Property Investor · Lakeland Florida · Member since 2026 · 4 posts · 2 votes3d
Congrats on closing. Two things I'd check before you buy anything else — I own and manage short-term rentals in Florida and manage properties in South Carolina and Georgia, and both of these have cost me time.
The master deed beats the zoning map. A parcel can be zoned for short-term use and still be blocked by the building's declaration or HOA bylaws. Those are a private contract between owners and they're enforceable regardless of what the city permits. I own four units in a building where the city allows nightly rentals and the declaration sets a seven-night minimum — the declaration wins. Get the recorded declaration and current bylaws before you write an offer, not a summary and not what the seller's been doing. A rule nobody enforces today is still a rule.
Check the conversion overlay on anything oceanfront. Myrtle Beach adopted a Short-Term Rental Conversion Overlay in late 2024 that runs opposite to most coastal regulation — in buildings of more than two units between Kings Highway and the ocean, units can't be leased for 90 continuous days or more, and back-to-back shorter leases to work around it are explicitly a violation. If you hold four oceanfront units and the market softens, the long-term fallback may not be there. Confirm the current text with city Planning and Zoning rather than a forum post, mine included.
One suggestion on the four-unit plan: consider buying them in the same building. One cleaner doing consecutive turnovers with no drive time, shared linen inventory, one maintenance trip covering several issues. Four scattered units is roughly four times the work. Four in one building isn't much harder than two. The tradeoff is concentration risk — one HOA decision or one assessment hits everything at once.
Also worth a call to your insurer before the first booking. A standard HO-6 usually isn't written for paying guests.
Happy to answer anything specific.
— Glen
- Investor · Get yourself trained before doing something inadvisable. · Member since 2024 · 3k+ posts · 1k+ votes3d
Quote from @Scott Floyd:
Hi everyone, brand new at this. Went a few STRs in the grandstand. I currently own a personal vacation condo in Myrtle Beach. Just closed 2 weeks ago. I'm looking to invest in my first STR by the first of the year.
Already have LLC set up, banking and business license. I've been using Claude to create business plan and run data analysis along with Rabbu on units that fit my plan. I plan to acquire 4 units over the next 4 years. I will be moving there full time at that point and turn our personal condo into the 5th STR at that time.
Any beginner tips, tricks, dos or donts would be appreciated.
Sounds like fun. Just be aware that markets change and it's always a good idea to buy with the backup plan of selling. It's expensive to sell and I'd go through the numbers just for the comfort of knowing what to do in the event things change.
- MD/DC · Member since 2024 · 1k+ posts · 1k+ votes3d
Expensive to sell and can be difficult with condos in particular due to multiples of an identical product for sale at the same time. Keep in mind supply vs demand re: occupancy is no joke. I have a 1bd 1.5 bath in one state that I charge more per night for than my 2bd 2.5ba townhouse, closer to the beach in a more affluent area in another state due to the large number of rentals. Not knocking it completely but just some items to be aware of. This might be worth moving to STR section.
- Real Estate Consultant · Chattanooga TN · Member since 2026 · 19 posts · 7 votes2d
Scott, one thing I'd put pretty high on the checklist before you start comparing potential STR purchases is whether the rental strategy you're underwriting is actually permitted at that specific property.
City/county rules are one layer, but HOA or condominium documents can create another one entirely. I'd rather eliminate a property early than build a revenue model around a use that turns out not to work.
Are you already looking at specific properties for the first purchase, or are you still at the market-selection stage?
- Member since 2026 · 2 posts · 0 votes2d
I am looking at properties. My goal is to close just after first of the year.
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