I think from an investor stand point if you can just rent as a normal LTR and be flexible with subletters in the summer months that is the easiest way to go. 

Normally they're very generic and don't really give you the info to be successful in your local market, or maybe any market. 

Then you work with your contractors as you normally would to set up rules of automatic approvals or running them by you first. 

Just do your normal cash out loan.Anyway, I hope all of that makes sense.  

You need to let your tenants do normal life things in the place they are renting.

I am going to throw this out there , investing is always a gamble , you dont always win .

If this is an insurance claim the process is very different than hiring a roofer during normal circumstances.  

Lastly there just is not enough of those type of deals to take on extra work and risk .. its too narrow of a niche.. and keep in mind my fee's FAR exceed normal HML fees they make it worth my while.

Because the Adjuster's fee is normally a % of your claim payment, you may want to get estimates of the rebuilding costs and see how close the proposed settlement is before you decide if the Adjuster is worthwhile.  

Look up Pace Morby and his groups, etc, they sometimes source homes that don't have as high of an entry fee as buying a home the normal way would.