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

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. 

I have since put everything back on ebay and have sold it all, getting most of my money back. ( Very proud of myself for figuring out a way for a broke *** red neck idiot, to get basically a free Real estate investing education which so far has made me a buck or two,)    :)     Even today when I feel I need to get current in trends and techniques I go to ebay for some easy listening material, but I've found that most of it is just rehashed fluff from the origional gurus from my early years.

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.

Investigate how to vet tenants properly, there isn't a one-size-fits-all approach, and the resources and limitations of your locality should play a big part in determining the technique you use.

From aligning contractors to ordering materials to handling issues that have arisen, I am incredibly involved in this STR-- it has not been passive for us whatsoever. 

There are useful techniques that cut the time down drastically and we offer insights in our list.

I would imagine you are incredibly busy with what you do for work and your own wine adventure.