I'm trying to analyze my first property and not sure how to set it up to run the number using the calculator tools here. 2 of the units are successful Airbnb short term rentals, and the other two units are month to month rentals to existing tenants.

If you're buying it shortly and THEN after you own it will it be ready and available for rent-the costs will be capitalized and accounted for with the basis of the property as well (when you eventually buy it). 

Most people are refinancing a BRRR because they are in short term debt (like 12 month hard money used for purchase +rehab financing) or own the property free and clear (they bought all cash) and would get a higher return on equity by leveraging the property and reinvesting the cash out proceeds of the loan to scale the portfolio. 

I have looked into the Pittsburgh market and have been there before, but just once for a short trip.

Short term rentals in St Pete are technically illegal but it doesn’t stop hundreds of other investors from doing it.

Maryland is an interesting case in that legislation has been introduced each of the last 3 years....but with the short legislative calendar from a part time legislature, its been hard to push things forward.

How come shortly after questions were asked that you could not or would not answer the website disappeared from the Internet?

In our experience, things move in ebbs and flows and the speed of rental depends on your asking rents relative to competition.For example, there was a period of several months at one of our properties when a 3 or 4 BR unit came on the market it rented almost instantly. 

If you are having trouble sourcing either over a years-long period I agree selling makes the most sense.

If you’re looking for short-term cash flow, you might need to explore nearby markets with lower entry costs and higher cash-on-cash returns, even if they aren’t as familiar to you.