But it, rent rooms, Fix it up. 

I do condo plans as part of my W2, and these SF calculations can vary based on the coord with the attorney and owner as far as how the association is originally set up in its budgeting for dues.

I don't require it through Airbnb, but I do through Vrbo, because they are notorious for not backing you up when a guest does a charge back on their credit card. 

To make up the difference of the total price, I used seller credits, lines of credit, and second mortages on other properties. 

I’d be happy to connect and discuss further—feel free to send me a DM if you're interested in setting up a call.

Are there any potential flaws in the way we are setting this up?

I use Proper insurance, unwritten by Lloyds of London, for my STR - covers the extra issues you would expect from an STR like vandalism, alcohol liabilities, business interruption up $10k, hot-tub cooties etc.

Then you'll need to find land, acquire it, find a spec home buyer and set up meetings to design plans or buy a set online with mods.

We do not accept zelle because of how easily it can mess up an eviction in Chicago.

Show up prepared, ask thoughtful questions, and take detailed notes.