Otherwise a surveyor is probably your best bet. 

@Sam Shin Not to be argumentative, but I bet you'd have a different opinion about buying in Hawaii if you had bought in 2006-2008 and were then forced to PCS in 2009, after the crash.

Some people bet on rent appreciation to eventually satisfy the 1% rule.

local banks/credit unions are your best bet. some will go above 75% LTV on SFRs, maybe even multis.

Dig into your sphere of influence to see who would be willing to bet on you.  

Or if its a mid size community the best bet is if the community has an elderly/disabled social worker you can invite to join you in meeting with her.Many on here will say you are not  social worker, just boot her and leave it at that. 

If you post where the property is located I'd bet someone ere would take a look at it and give you some ideas.I'd take care of the roof and then work on getting one unit rehabbed and rented then repeat the process. 

I live in Northern Virginia where deals aren't typically amazing so my understanding is the best bet is buy and hold since I'm in a pretty stable market.

By the way, there are many other fields where you can pay for a training class and the job prospects are questionable....I see ads for learning to code, and I have no idea what the classes cost or whether they pay for themselves, but I am willing to bet that many people are not cut out to write software, but whoever is offering the class will still take their money.

Best bet is to get him to sell it at market price.