That is some great awareness @Adriana McLaughlin...to realize leaving the W2 may not be right for you.  

You now have $5k in unreimbursed expenses, and 2 houses; one with a $200k mortgage worth $250k (giving you $50k in equity), and; one with a paid off HELOC, value and mortgage unknown, but presumably with more than $165k in equity.You should also treat the $5k unreimbursed renovation cost as a debt and pay it back (even to yourself) accordingly.There is no tax due because not only did you not make any realized gain, but there was no sale. 

Doubt you'd get any repeat guests once they realize the water is brown from Rig City.

I had a bit of realization yesterday and want to test the temperature, mainly for self managers and smaller PM's. 

There are so many issues with what you just said.First off, when you say “spent” all your emergency funds you do realize you can take it back out with the HELOC strategy right?  

I will admit when I had my first investment property at 24 that I did not realize all the legal aspects of RE and all the laws concerning what you can and what you cannot do.  

What most towns don't realize is building has a greater impact than STR, the increase in population means you need more properties to house people.

Once I booked and realized that, then I was stuck - waiting... to see if I would get a response in time for me to check in.  

The first thing you need to realize is that this is a STR business, not an Airbnb business.

Physical REI is not a paper investment; almost anyone whose invested on paper numbers I am willing to bet is showing a lot less than the reality of if it unless they took realized gains by selling(into the appreciation rate) or cashed out refi.