This can be a difficult and slow process with limited capital so start it sooner, rather than later. 

But from the groups that I've joined everyone says that Portland is too difficult to manage a rental.

They are taking all the risk with no premium for the higher risk deal.It is not that sellers financing is impossible in a sellers market, but trying to do it at unreasonable terms for the seller may be difficult.

It can still be month to month, but now it will be written out, you will know exactly who is there, where they work etc etc.Nearly doubling their rent to market is a bit much but if you went to say $1000 now it would be difficult to go to market in 3 or 6 months.What shape are the apartments in?

He's unmarried and and just five years out of college, he's living in young 'hip' area,  his rent is under market and it would be difficult to buy a property in his area that would cash flow as a rental so it makes sense for him;  I think in the situation you described it would be a reasonable thing to do as well.

If you get a 15 year loan, your interest maybe somewhat lower, but cash flow will be difficult and you might regret it later.Personally, I get the longest amortization period possible, and never regretted it.

It was a disaster for him and he showed his shining true colors by the way he dealt with investors through this difficult holding period.

Question is, how difficult is this going to be for me to enforce any of these since I don't technically own the property?? 

REO standing for Real Estate Owner(by the lender) It is pretty difficult to buy these properties directly as an investor, as the lender wants to sell this property for as much as possible.

It may be difficult to prove discrimination based on this but it certainly opens up the door.