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. 

I knew I could do alright just renting it and that was my fall-back (and what ultimately happened), but I didn't know if it would be a good enough deal to interest turn-key buyers.  

The window unit you had when he moved in, should be good enough, unless it does not function as it did.However, there are larger air conditioners and there are fans to help circulation from the other rooms.

If the deal is good enough you can find an investor to buy it without inspections. 

Too many owners want to replace things that are good enough or before they wear out.

which make no mistake, you have to train the Va on the specifics of your model.You should do your own cold calling until you are good enough to train by example.