Maybe it is more difficult if the damage was more serious like fire or flood but it goes same with any insurance claim.

I would decide on what strategy you like more.

Do any of the tenants have Dogs (Breed restrictions are individual to each company).These may not prevent you from getting insurance but they may limit the number of companies willing to insure it.

First off, I really like how you’re thinking beyond just the renovation.. you’re creating a tailored investor strategy that builds excitement around upscale features.

Is there a good strategy to scale my investments or should I just keep what I’ve got?   

Liability insurance covers negligence.

They have the choice of finding their own insurance or they can be automatically enrolled in my master policy.

There are opportunities out there but some strategies are risky. 1 - Airbnb (STR) comes to mind - very competitive, very saturated and becoming highly regulated.2 - Most STRs are transitioning to MTR so that market will be saturated soon if it isn't already.3 - Insurance crisis in florida is getting bad so those costs will eat up cashflow and short term appreciation.

Hopefully your lawyer also mentioned insurance- title and hazard.A quitclaim deed transfer can hurt your title chain and title insurance. 

Frequent hail storms pushing insurance rates up in that market.