Every decision you make with regards to every deal you make should be made based on the next move you are going to make, which is dictated by the REI Plan you've already designed.Your next move is to design that plan.

Besides legalities, is cost and ROI the driving factor in the majority, if not all of your repair and upgrade decisions?

Every decision you make should will be based on that specific "next thing" you will be doing.

This is a tough decision for first time home buyers.

If you have not looked into those options before, they may be able to give you some perspective when making your final decision.

The other big underwriting decision with commercial lenders is your DSCR.   

One of the biggest advantages/skills that we all learned in the military is looking at the second and third-order of consequences (If I make this decision, it can result in x, which can then result in y).

I am from north of Orlando Congrats on your decision to get your real estate license.  

I let my STR PM deal with these issues, but if I were to make the decision (I do not, the PM handles this without involving me) I probably would credited you half the unit cost for a future stay (assuming it rented for the days you had booked) and refunded all the incidentals. 

However not yet a decisive one...Fortunately (and unfortunately) I am a dreamer with many interests and skills.