First it sounds like this may be a "heavy rehab". 

I see some conservative areas here who would traditionally support private property rights coming down heavy against STRs.

If you need an option that isn't as document heavy, a DSCR cash-out might be a viable option if it's an investment property.

Ft)Heavy Cosmetic ($60 x Sq.

diversification and cash flowSan Jose, CA has been very appreciation heavy... and i'm not opposed to keeping some property here, though the multi-family / commercial real estate has very low cap rates, and low growth from what i'm seeing.

I was heavy in RE but sold most in 2021 and appreciate the simplicity of a Vanguard TSM account as I head into the last 5 years before retirement. 

Southwest Florida is definitely an exciting (but competitive) market, so props to you for diving in!

Went a bit heavy on the annual taxes due to the increase in the area the past few years.

Quote from @Brandon Weis: In your opinion, as you are starting out at 0 reviews, do you think it is a must to beat the competition on price to overcome customer's hesitancy or lack of trust with no reviews?

Put a heavy emphasis on who you choose as an agent.