Property manager explicitly said no one has been on the roof other than the roofing company, and even suggested I look into an attorney to go against the roofing company.

very simple go to the county planning department office show them the map and ask them if surface drilling is allowed in their zoning code..

Instead, he suggested I find a GC that's willing to enter projects in a "supervisory" position.

While the IRS does not mandate a physical site visit, the IRS cost segregation audit technique guide (ATG) does suggest conducting “field inspections.”It’s important to note that the ATG is not an official IRS document.It serves as a guide and cannot be used, cited, or relied upon as an authoritative source.However, the recommendations in the ATG are worth considering.According to the guide: “A field inspection is recommended to document the physical details of the building, type of construction, materials used for construction, the assets contained in the building, the size and types of building systems, and any land improvements that were included in the purchase of the property and the condition of that property at the time of purchase.”So while the IRS does not require a site visit for cost segregation studies, following the guidance from the cost segregation audit technique guide can be beneficial.

It’s $50 and super simple.

Any suggestions?

I would suggest going local first, if you can't locate a local lender that meets your needs, try the DSCR route.

What would you suggest as a number or percentage after the refi/sale that would make sense for the lender?

Looking for any suggestions for insurers who will insure a high value, older "fix-n-flip" property in St.

I suggest looking into real estate meetups near you / your markets of interest to start building your team.