And perhaps I wasn't clear (or perhaps you read too quickly), but I'm actually mailing the probate leads a series of white, professional letters that I'm doing myself (at this point) because I think it's a good mail piece and I couldn't find something I thought looked good enough online.

My goal is to be in and out in 15 minutes with a number that is good enough I can make an offer.  

If any of the houses are in a good enough shape to still be usable as rentals, you would sell as a rental property as that will get you a higher price.

A small chip in the bathtub and that’s a fail, window doesn’t open good enough that’s a fail, bedroom door lock doesn’t lock properly that’s a fail.

I’ve considered it before, but the city worries me greatly…I might be convinced if the deals look good enough.

Cozy was "good enough" for awhile but the lack of a mobile app and multiple tenants having issues setting up payments, etc caused me to look elsewhere.  

This still usually isn't good enough for most title insurance companies but it gives us merchantable title to legally possess and or sell the land.

I would contact your agent first if no solution get in touch with the insurance company. send pictures of the roof and show them it is in good condition and see if that would be good enough, if not see if they would agree to a roofing contractor inspecting it and doing the recommendations they suggest. 

If he has a legitimate special circumstances case he can proceed with his plan just fine after informing the lender, if he doesn't have a good enough case he could face criminal prosecution (it is unlikely but possible) to save a few hundred bucks a year instead of just waiting 6 months and fulfilling your occupancy condition.

As long as you have a deal that is good enough you should definitely be able to find someone to fund it.