From there you should be able to calculate your net operating income (NOI) which is the income you earn before paying any debt service assuming you are financing the investment. 

Chris has NPNs in judicial FC states so when he says that DC is the worst, I'd like more details :)We operate in IL and NJ (not PA or NY).

@Kevin Scanlon , @Tyler Hespeler, @Francois Martin  all own and operate STRs in the Eastern part of CT.

These guys do and they also own the operations of their business too and continue to grow it. 

I'm currently working full-time in the military (National Guard) as an Operations Officer and loving it.

@Jonathan Bell This group has many well established, experienced multifamily investors and operators.

They had a home based business and its kind of iffy when it's operating in a residential zone.

I don't know the deal and suspect you are trying some Airbnb or resort operation but if you look at what actual resorts sell for and how much more value you get in buying a resort, you will see why this sounds like a stretch paying full retail for 4 different condo units.  

Honestly, I'd just go directly to the lawyer and they'll be able to take it from there.For us, we filed a multi-member LLC with the state first, then went to a lawyer to structure an Operating Agreement.

The details might vary, but this is how most private money lenders operate.