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.

If you go to a bunch of banks and it isn't working out the best bet would be to keep educating yourself and socking away thousands every year from the GI Bill.

I am in the confirmed-bear category, so I wouldn't bet on it.Don't get me wrong.

Your best bet is really look at the market for SIMILIAR CONDITION units.

Your best bet in getting business credit doing this is simply with the institution you get it with.

Prices in Hawaii are very similar to those here in San Diego, but I bet Hawaii would make for a great place to invest in vacation property.

I'm not an attorney so please consult with a local RE attorney, but I think JV is your best bet when starting out.