Umbrella Policies are good, but they are not an asset protection tool, they only cover litigation/damages after you’re already in litigation or found personally liable.

And, voilà, you have your own guide.Problem is what they'll likely want to know will probably be basic and already covered by those guides.

Or maybe the units aren't equal and one rents for $2800 covering most of the cost of living there. 

Check out this site - https://theluxurypergola.com/blogs/louvered-roof-info/hurric...They cover wind resistant pergolas in general but I would make sure whatever you get will be able to stand up to hurricanes that happen there from time to time.

My goal is to live in the home during the winters, maybe 3-4 additional weeks for vacation, then rent it out to help cover the mortgage the rest of the year.  

I am guessing they probably raised $15-25M from investors for the deal, so while the bank would still be covered investors would appear to collect maybe 10-20 cents on the dollar if they were to liquidate.if that's the case then I don't see buying one year really does anything unless I am missing something ? 

The condo fees cover pretty much any maintenance / repair.

We also require that we be added to the contractor's insurance as Additionally Insured, so we're covered if they cause damage or liability issue.3) If the property is occupied:- One of our people MUST accompany their person (and we charge for this). --- We were sued many years ago, along with the owner, because tenant claimed owner's contractor sexually assaulted them!

Maybe even offer to cover some closing costs to sweeten the deal if they’re stuck on a higher price.

I will PM you my rep -- they are in Indianapolis, but if they don't cover your territory, I am sure they can send you contact info for someone.