[SuperUberBob]

Well, you have to call preflop now. 550 into 2K+ pot.

You're in an interesting spot if you just flop top pair. If you check, he probably shoves and you'll have to decide whether to call with top pair/decent kicker. If you bet out and he shoves, you'll have to call because it won't be much more to call.

Since he re-raised to 1000 and now only has 2250 left, you have to believe he's getting the rest of those chips all in with a pot like that regardless of what hits on the flop.

I think an open-shove would be an okay idea if you flop top pair. Put him to a decision because if you don't, then he'll do the same to you.

So, if you flop top pair, your top options are check/fold or open-shove.