I'm not sure what range to give him after he calls pre-flop. QJ seems v unlikely ... TT-QQ seems most likely, maybe AQ. You must have great fold equity against this range if you've been reasonably sane (ie you've represented AK, AA-TT).

So I tihnk I'd just lead. If he makes a suspicous flop call, there's a good chance the turn will get checked along.

I reckon with this range he'll check behind if you check, but then you'll have trouble getting TT-QQ to fold, so you have to hit your hand.

Also if he does bet, I suspect he'll call your check raise.

Overall, the CRAI just seems too greedy.

[EDIT] I guess we'll find out what he had even if he folded!
[EDIT2] Also time for a new UB screenname

I take it you have no FD to go along with your SD? Based on that if you lead $120 and he puts you AI you are getting a little better than 1.4:1 so that's not the way to go(at least according to the numbers). If you lead $350 and he puts you AI you get 2.1:1 so around $385 is your break even point. Do you want to over bet the pot that much? I think it shouts draw and to be safe, numbers wise you would want to bet 25-50 more which is a much bigger over bet. On the plus side you may win it right there. You would be a much better judge of what that size over bet represents than I. That's what you need to bet if your intent is to follow through on the hand and protect your draw from being overpriced.

I think that play is wrong for a number of reasons; your draw may be very vulnerable to redraws, for example, and you pay a huge price just to be a dog to most of what he calls with. I like checking and if you are determined to CRAI then so be it. If he wants to protect his stack he will also have to over bet this pot to make sure you don't have odds to chase. You are about 31% to hit your straight if you draw 2 cards. That's 1-2% better than having AKo vs. KK with 5 cards to come except we know we win if we hit there and you may hit and lose here (whether the amount of times that happens is statistically relevant or not is another thing, I doubt it). If you check and he doesn't over bet you will often be getting odds to call unless he decides to give it up cheaply and nullify your effective IO but then you win the pot right away with your next bet.

I think reraising preflop here in this spot is not too good against taylor. I really think with position his range for calling a reraise is very wide (ie. 76o) as he is very competent and will end up putting you in tough spots on a LOT of flops.