Glad to see you wised up before you threw your money into expensive toys like myself. 

Florida is a reciprocal state to Connecticut for licensing so I was toying around with the idea of getting a Florida license as well.

If you have a lower gross rental income per bookings (say $150 average booking for a small condo) and a similar $20 cost per basket, but that basket includes nothing that is tied to the identity of the property or makes it unique, it seems likely the repeat booking rate and likelihood of positive review will have minimal impact.

Hello Everyone,I'm toying with an idea that I had today and was wondering if the forum would help me shoot holes in it.  

This rule is unique to 3 & 4 unit properties.

Indianapolis is unique, it can change block by block.  

I've been toying with the idea of getting into rentals as some more supplemental income, and although I've struggled with the math as far as justification, i believe the main reasons folks here by rentals (please correct if I'm wrong) are: Cashflow (although I've seen people do deals eg on Roofstock for only $100-200/mo) + appreciation (when sold) + taxesSo assuming I'm correct there, then the potential tax benefits are 30% of the reason to do rentals.

In other words, seems like a unique way to increase the value of the two buildings by consolidating them as one entity.So of course first you'll want to find a real estate attorney with experience specifically in deals where the seller holds the note. 

This is a unique situation trying to loophole around the capital gain exemption rules for personal residence.

We have some unique hybrid plans for unique/smaller portfolios...really the goal is to always make it a win win and essentially make sure by adding management it will increase revenue that exceeds cost or of course free up owners time to be 100% hands off.