However, I recognize I still have much to learn.I would highly value advice from veteran investors on finding the right opportunities, understanding regulations, financing projects, and overall best practices.

Hmm....I'm thinking about that...because I have a family member who have a rental in the Fort Lauderdale area with a beautiful oceanfront in a flood zone area and her place is in high demand.

How is one able to do data to see how other STRs are booked/performing in that month?

Even tho in our opinion the current “fair market” rent is pretty high and not justified long term. 

(The fact that they have the nerve to call it a "High Yield Savings Account" is almost insulting! 

The quote I’m getting is for 4200 and that seems a little high.

I have a real estate portfolio with good amount of equity (most of the portfolio is free and clear), however my personal DTI ratio is too high and that's stopping me from tapping into it to settle some debts and buy more properties.

I need to pull out cash to perform maintenance on the same property.

There is also a large restaurant company here that I have been told needs rentals for a shorter term but pays very well to house staff that they bring in from out of town to work for them during high season.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+, zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680, some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.