The previous owner must have been upset about his/her loss because there were holes in almost every wall, lights pulled from the ceiling, appliances damaged, etc. 

I want to purchase a property that has an old roof that will eventually need replaced I’m wondering if it would be covered under storm damage even though it would be a newly purchased rental property 

Example, the water heater leaks, create damage, mold, remediation, etc.. what they will tell you, you should replace or performed preventive maintenance on the unit, no proof of it.

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."