Odds are, only the W2 job will be "counted," but I can't say for certain without all the information. 

There is no perfect investment strategy however by buying conservatively the odds can be more in your favor than buying under conditions where everything has to be perfect to do well.    

If you were not receiving rent it seems odd you would not be asking the PM to file for eviction.

I must still report the full $200,000 on my taxes and can't take the $40,000 as a deduction - which seems odd because the lawyer will also be reporting the $40,000, so it appears that chunk will get taxed twice?

The whole scenario seems odd. 

It is not unheard of, but I'd imagine it to be a bad business practice not to allow flexibility if it spoils the deal. 2% buyers commissions in my area are very rare. most are 2.5-3% sometimes subtracting a small transaction fee (something else that is odd to some and common to others).

which is very odd!

Did you go see their dorm room and determine if they were like Felix Unger or Oscar Madison from The Odd Couple?

By working on the deal (funding or making) you can stack the odds of a successful outcome in your favor.Best of luck.

@John Woodrich His parents have done flips and he's done hands-on work (he's 25-ish) and he'll be the buying agent, GC, and selling agent, in addition to bringing 50% of the cash funds (I'll be bringing the other 50%) Yeah, that Check part seems odd so I'm balking at that for now, as at this point we're not writing enough offers to justify sending EM.