He is currently working a hail storm in Dallas and will be back in Oklahoma by the end of October.  

I have a lot riding on this so please only answer if you are fairly certain about your answer.

Since you're a short bus/train ride away, I'd make a weekend out of it and visit the neighborhoods yourself.

I warn that they must have the means and fortitude to ride out the down cycles otherwise they can sell low and lose money.I have purchased a couple times at near market high times (1992 and 2003) that had the properties initially lose value (the 2003 purchase at its low was down more than $100K). 

I've had full ride scholarships the whole way through and had passive income that paid for living expenses so I didn't have to use loans for school itself. instead, during undergrad, I used subsidized   (interest doesn't start accrue until 6 months after you graduate) loans at 3% to pay down the principal on a mortgage I had on my first rental property which was at 6%.

The fix up and finish out depends upon the strategy whether it be to hold (which I always suggest to ride out the economic corrections) or fix it up to sell it.

What that means is you basically ethically bribe the tenant to accept a few thousand bucks from you in exchange to get out in 30/60 days instead of riding out the lease.You'll have to do the cost benefit analysis though: are the rents so low that waiting 6 months isn't the better option?

Sending out 100 letters in a competitive market and hoping one will be a deal as someone starting out, is like throwing a hail mary.

I actually switched over to driving a limo giving me more down time between the rides for a better pay and miles on my own car.To not pay half mill for a place in Studio City is going to be a tough find Id think.

As far as PSLF, a decent number of hospitals are 501(c)3 so if he can land a job there he can ride out the 10 years.