[Man of Means]

It seems like you made this play with hopes that he'd bet and then fold to your raise. Do you have a particular read that this is likely to happen?

I'd rather check and call the flop. This way you are assured of some value and at the same time the pot stays small.

The problem with the checkraise is that it puts you in the middle ground - if you bet the turn you're either going all-in, you can play possum to catch a bluff (need a solid read for this) or you have to check/fold at that point.

That said getting all-in here isn't terrible if you think he'll call off 100bb's with 99, JT, AK etc. Very rarely do you find that player though.