Everything I've ever heard says not to play the appreciation game and speculate.

@Derrick Thomas,Unless it was the exact same lender, deal, financing, etc, I don't think you should play the discrimination factor.    

Don't bother house hacking at this point, play the rental game... till you're done with your reduced or free schooling.

Just remember it's fun to dream but whether you buy 5 tickets or 200 your odds to win stay about the same.So just drop a five or ten on it and nothing else.I only play the lotto when it goes above 200 million.That keeps me playing it just for fun on an occasional basis and I never usually go above 5 dollars in tickets.

Selling the cute little rental could mean some debt reduction and other opportunity, or it could mean disaster, if I dont play the cards exactly right I will not be able to afford my own home mortgages.  

(my dad loved to buy and sell with seller financing so it is a super way to play the game!

Trying to play the role of inner loop snob.

It can be frustrating to play the waiting game but it just makes it that much more worth it when the right property comes along.Don't forget that your first property may not be your best deal.

If you want to play the nice, generous, host and try to get a good review  (which is not guaranteed given the type of guest you describe ), or be strict on the principles and wanting to give them a lesson.

Play the law of averages.