Any clue what I can expect timeline and court/attorney expense wise if squatter fights it to the end?

So, not only are you getting access to the NWMLS to search properties and find deals, but you can also add value to your sphere of influence with your capabilities as a broker.

Not everyone is capable of the responsibility of home ownership.

It's just that two friends can fight and one could straight up leave.  

This means your tenant is going to show up in court and fight with you to get the money.

B/C occupants fight like anything to stay out of D class (so you get some lower beta play here).  

Stay away from rent credits, instead use a lease plus the right of first refusal then..March the buyer down to the bank to open up a savings account to save 3% for FHA or 5% for Wells Fargo, work on their credit to recognize credit  work on their credit through our capable credit coach The deal is they can buy it at any time for a new appraisal price The situation with options and government loans are screwy, just offer the ROFR and be a good landlord.

Maybe I should take a leap, but honestly, I don't feel that anyone in my immediate circle is capable of financing a substantial amount. 

I feel like these should not be our responsibilities, but my roommate and I agreed to pay for carpet cleaning so that we wouldn't have to fight our landlord.

We will be investing from out of state, a rock star property management company capable of managing and overseeing this kind of asset is of the utmost importance.