[gumpzilla]

You're essentially competing for the last spot with the three shorties. You can't wait for them both to bust out. 2-3 times per orbit is definitely enough to know that this guy is opening with a huge range. Eyeballing it, it looks like he'll be getting 2.5-1 or so to call, so I think you can continue relying on him to call with ace small.

If you push and win, then I think you're probably 90% or so to get a seat. If you fold, I think you're 40% or so to get a seat. Given this, and given that seats are the only prize, you need to win more than 4/9 of the time against his range to make this profitable. That's not very much, especially against a loose raiser. Any sense for what a good range for him will be? I suspect it's tighter than any two.

One thing I'm neglecting in my analysis is the odds of the BB waking up with a big hand behind you. There are two possibilities: 1) BB calls your push, hopes that chip leader responds in kind, they check it down; 2) BB requires QQ+ to get involved here and pushes over the top. 2) is obviously not that big a danger, 1) would depend on my assessment of BB.

To summarize: I think I'm pushing with a lot of hands here. The specifics would depend on a reasonable range, but as a guess, I'd probably be comfortable pushing 44+, A6+ and probably a bunch of suited broadway hands.

EDIT: I've completely neglected the stop-n-go issue, but I think I prefer pushing. 99 is going to perform well enough against his range that I don't mind getting my chips in, and I'd rather get his stack (as I mentioned, I think he'll call getting 2.5:1 given how you've described him) (and by his stack, I actually mean the relevant portion of his stack) than give him a chance to correctly fold or call on the flop.