I think it's healthy to question the way you play and try to improve. But I also think that this is an easy push.

The likely outcome is that you take the blinds and the bets from the limpers.
There are 3 people to act after you. The likelyhood that one of them has JJ+ is a little over 5% if my math is right. I'll assume that they'll all call with JJ and fold 99.
Let's say you'll get called by AK as well. The odds that one of them has that is 3.5%.
I'll ignore that one of the limpers could have a monster here.

So there's 91.5% chance they won't call you and you win T700.
5% someone calls with JJ+ and you're about 81% to lose T2480 and 19% to win T3180.
3.5% someone calls with AK and you're about 55% to win T3180 and 45% to lose T2480.

Combined EV = .915*700+.05*(.81*-2480+.19*3180)+.035*(.55*3180+.45*-2480) = +T592
If you think someone might fold JJ or call with 99- or AQ, then EV is larger.

Your roommate will argue that his play has even greater EV. I don't think so. In the AA scenario, the BB will either reraise you all in preflop or smooth call and put the rest in on any flop. Will you fold any of those?

Playing TT after a flop isn't going to be nice either. Your stack is so short that you can't really get any more information. And one or more overcards will flop 70% of the time. An ace or king will flop 42% of the time.

So keep it simple. Take the T592 and run.