You will want to make sure you are installing something new that provides the right solution not just putting back something that matches but doesn't do the right thing in the first place.You may also want to consider rain gutters because doesn't look like the roof has much of a drip edge. 

I do know of some builders and lenders in the area that are organizing to create solutions for people who are stuck because a builder can't finish the job. 

Hostfully is more robust and a more complete solution to Hospitable.

But organizing those vetted people is a HUGE portion of your solution.  

We do Annual Evaluations/Walk-thrus to monitor tenant damages.

open to other financial creative solutions I may not be aware off.

He’s affiliated with Dave Ramsey solutions but I think that is a benefit in my case.

It's not ideal working in multiple systems but it's the most cost effective solution we have found.

Everyone recommends Quickbooks, yet it is not a one-size-fits-all solution esp. when its annual price can be $1000+.

If you run into challenges, call a different independent insurance broker - they usually rep numerous companies and I think you will find a solution.