Hello everyone, my business partner and I are about to buy our first short term rentals at the beach in Maryland.  

Hi everyone,I’m looking for some guidance on the best way to structure my business entity for rental properties and would love to hear your experiences or advice.I live in Texas, but I currently own two long-term rental properties in California.

So if you have one long term rental and one short term rental, it can be difficult.practical example: you have a long term tenant that stays for 365 days.

That’s a solid move — taking a property most would overlook and turning it into both a profitable and purpose-driven asset.We’ve been doing something similar through our Home Asset Conversion model, helping property owners reposition underperforming real estate into veteran and senior shared housing — with long-term leases, stable cash flow, and huge community impact.Sober living, senior living, and veteran housing all share that sweet spot: high demand, low supply, and mission-based investing that still hits strong numbers.Curious — did you self-fund the rehab or structure it with a partner/investor model?

The lake house conversion idea has potential — but tread carefully.If they carve out 2/3 of the property into a short-term rental, they could qualify for STR bonus depreciation if managed as an active business (not just passive).

Investment also spiked in Class A Short-Term Rentals (STR) and investors started paying higher and higher prices based upon anticipated STR rental rates, that exceeded sustainability based upon Long-Term Rental rates (LTR).

To apply this in real life, last week we helped a client put a 1 bedroom cabin about 400 yards from the edge of the Smoky Mountain National Park under contract under $200k, the expected return from a cap rate, cash on cash, or IRR are all deep double digits.If long term appreciation is part of the goal, I'd want to understand long term migration patterns as well, and look at regional parks near places where there is a lot of people moving within 200 miles. 

Lenders like well known tenants with good financials and long term leases if possible. 

This can be especially powerful if you qualify for Real Estate Professional Status (REPS), Short-Term Rental (STR) classification, or Active Participation, since those statuses can allow you to offset W-2 or business income with real estate losses.So whether you’re thinking short-term resale or long-term rental, the basement gives you some nice flexibility from both an investment and tax angle.This post does not create a CPA-client relationship.

College Park can be great if you’re open to student rentals or short-term opportunities.I work with several investors in those areas on the tax and strategy side — happy to share what’s been working for them if you’d like to connect and swap insights.