I started off with the standard turbo tax for 1099s and it felt limited.

What started off as primarily a second home with the possibility of short term leasing quickly flipped to a STR first and a second home when not rented because demand is so strong right now for STR's in this area. 

Did you write off those special assessments in 2010 and 2012? 

I haven't walked most of these properties in person so my rehab numbers are based off the pictures, but it definitely seems like there's some value to be had here.

- Renting it Out: The likely rent I'd get in this area will cover half my mortgage payments at the moment- Add Square Footage: Taxes will likely go up significantly- Build an ADU: Overall ROI will likely not offset much since it'll still be counted as value tied to the one house- Selling Off Land: Sits on .5 acre that I might be able to sell.

Appears the guests may have left the faucet "on" when the pipes were frozen and when no water came out, forgot to turn it "off".What may have caused the overflow of the sink is maybe the drain lines were also frozen?

Our occupancy during our off season is near zero.

You are off to a great start with your first one that cash flows. 

Nothing builds credibility more than telling your lender that they are protected with loan documents you got from a stranger off a website.  

It appears some of you are giving off negative shade here.