Your feedback will be incredibly valuable to me, and I'm eager to hear all sides, positive or negative.Thank you so much for your time and help!

I thought it was incredibly hypocritical when I worked for a bank and got those requests from "risk management".

I cash flow about 300/month because I pay for internet and water (long story on the internet part), yes I know I could increase the rent, but not yet.

It's an incredibly thriving market.

We fought for this for several reasons: 1. tourism is our main economy 2. there are an incredible amount of dilapidated homes that could be renovated and made beautiful if the investment return justified it (which STR in a beach town could) and 3.this is a family-friendly, lower-cost and now COVID friendly way to travel. 

If it were mine I would replace the roof, including any roof decking underneath the shingles that need to be replaced, and look into the cost of doing a ridge vent at the top.As far as the air conditioning system , you might be replacing a well built heavy duty unit with something that has a much shorter service life and instead of using freon it uses some incredibly expensive chemical . 

Development is one of those plays that either goes incredibly well or incredibly poorly.

its the internet and BP your going to get all sorts of different advice..

I would not offer internet.

At the time there were no forums or internet groups to help and I did not know better.