An example, a small down payment initially, but the note has now seasoned for 60 months with on time payments documented by a third party servicer.

Definitely not doing the work myself so it sounds like resale value won't be impacted if I have a licensed person fix the issue and provide evidence/documentation that it was done correctly.

An architect can assist you in the initial work to get this submitted to the city for review and approval, and then a GC can pull the permit and work with you and the local inspectors to get this up to code.

But I was also sent a document stating that a county housing assistance program was guaranteeing the tenants security deposit (which was accepted by the current landlord) but not for the full lease term because the tenant is no longer receiving assistance and that the guarantee would only be until 2/2025. 

Code Enforcement in my market has just recently started, as part of their tenant turnover inspections, to document the material composing the water inlet pipes where they enter into the basement. 

Find a realtor that will submit the offers and lower your cost basis enough to where your returns get a bit of a bump. 

And, you need to cure your liability (you cannot use a city easement without obtaining a Grant of Easement from the city - a legal document to be filed with the Clerk of Court).You've done everything you can to mitigate the damage to your home and I applaud you for it.

Also, ensure their 2-year workmanship warranty is documented with clear terms.Shingle warranties can be worth it, but claims often hinge on having all the right paperwork.

I have attached documents that provide additional details to my post.

DSCR loans are widely available to first time investors, but they are considered business purpose loans and you will be required to sign documents stating that neither you nor any family member will occupy the property as your or their primary residence as long as that loan is in place.