Where does replacement insurance fit into this for both the homeowner and would-be buyer/wholesaler?  

To form an LLC or S Corp, or any other entity - you should be speaking to your real estate attorney and CPA to discuss what you will be doing, how you will do it and then they can properly advise you as there is no one size fits all.Generally speaking, an S Corp is better for flipping (or LLC with S Corp tax election) but again, speak to your CPA.The above is not to be construed as tax or legal advice.

I am trying to get my list of potential contractors now, so I can have some rough estimates, sift through the ones that aren't a good fit, and hopefully hit the ground running, should I find and close on a property.

You’d be wise to talk to many lenders @Jackie Garcia and maintain a stable of lenders you can pick and choose from as your properties, and their lending criteria, fit.  

I know they currently have a Duplex they just finished, and they are working on a 5 plex, but I'm sure they have several other projects that might fit your needs.  

I met an agent (let’s call her Sandy), decided not to work with her bc I didn’t feel like she was the right fit.

What is considered a good Cash on Cash ROI for the BRRR strategy or is the right number for this also falls into the category of "no one size fits all".

Lastly, I am working with a contractor, should I send him to every house that fits my criteria and to get estimates?

He’s trying to justify it by saying the property doesn’t fit his needs because of parking but I believe it’s just he can’t afford it. does anyone know the eviction process in Florida.

I recently have been in touch with some realtors who send me properties that fit my criteria as soon as they hit the market.