I never recommend to my clients to be the ones to deal with the tenants unless they have the experience.2.

Do you have recommendation on Agent who can do this?

Does anyone have suggested property management companies they've used in Florida that they can recommend I reach out to, to see if we're a good fit for each other?

Honestly looking at your situation I'm not sure I would recommend you do the taxes yourself,  change of accounting method (F 3115) isn't easy for someone that hadn't done them before these online software companies make things seem easier than what they are, they are good for less complex situations. 

I highly recommend the book real estate by the numbers.

The state will get its pound of flesh and my liabilities were better managed by executing perfect permitted work and excellent insurance.I'd sincerely recommend having a savvy CPA, Lawyer & Insurance broker.

As a side note, and maybe others will recommend this as well, obtain your real estate license instead if you are interested in pursuing sales full-time.

My wife and I started managing more properties for others as word of mouth recommendations started and we started to use the management and arbitrage cash flow to acquire our own properties and fund the BRRRs we were working on.  

Does anyone have recommendations for a contractor for an almost full gut property in Rochester NY?

I'm sure you have a great read on your local market but I'd recommend refraining from pretending to be an expert on a market you clearly know little about.Good luck!