[soah]

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The rest of the table quickly folds back to OYKP. He hems and haws, plays with/counts his chips for about 90 seconds and finally says "I'll gamble" and calls. I put him firmly on a pair of TT->QQ, probably towards the lower-end as I suspect he'd just stuff it in with QQ.

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Why don't you think AK is a possibility? You think he'd push with that, or not take so long to call...? Based upon what you wrote, it seems like he could very well be deciding to gamble by trying to flop top pair against what he thinks is QQ/JJ or something. Maybe he has AQ? I'm just not sure what leads you to put him so firmly on a pocket pair.

Even betting as much as half the pot is putting him nearly all-in, but a bet at that size would still leave you some stack left against the other player. If you bet $300, would you be able to read the crazy guy well enough to know whether or not your hand is good? If you check the flop, would their turn actions tell you whether or not they have an ace? If they'd bet the turn with an ace or better, but check without, then your best move might be to risk a free card and see what happens on the turn.