One of the most damaged properties I've ever purchased - perhaps the worst.

That will improve your bottom line and your profit margins.Vinyl siding isn't my favorite either, but the "damage" is done and I wouldn't go messing with it on a property with such thin margins.I also wouldn't call it free.

It seems to be one of the more stable (and affordable) areas to jump in, but yes, there is always risk.Colorado Springs, for example, has had 2 or 3 years with significant home damage due to fires, floods, etc.

Options I know of--1. claims adjuster plus insured appointed contractor--walk house together assessing damage and creating quote.2. claims adjuster and insurance company relationship contractor--same processI am sure there are a lot more ways it could be done, unfortunately, it is a process independent agents are not privy to.  

IMO, you have become myopic on the money and lost focus on the lease and control of the tenant - - you've abdicated control to the tenant.Security deposit IS NOT the last months rent or any 'bank' to be used to catch-up; it's to offset damages. 

It is over the top for your class of tenant and believe it or not they will damage it.

I think you may want to check out Brill's "Law of Damages."  

Property was left vacant and suffered freeze/flood damage.

Sub-roof damage repair?)

There is a little flood damage, but with a relatively small amount of capital an investor could really profit off this deal.