(bad/ok/good?) squeeze/value play

Riddler is a solid tag (ie has a wide range to raise otb). HansVK is a laggro donk (like 45/25 pre but taggish in bigger pots). I reraised him a few times earlier when he raised pre and he folded each time, but otherwise I have been solid/tag.

Hand #37040189-53359 at Columbia (No Limit Hold'em)
Started at 15/Dec/06 22:31:45

HansVK is at seat 0 with $111.70.
Hero is at seat 1 with $104.20.
Resindog is at seat 2 with $97.45.
cooner is at seat 3 with $43.85.
bigben80 is at seat 4 with $98 (sitting out).
Riddler32 is at seat 5 with $70.25.
The button is at seat 5.

HansVK posts the small blind of $.50.
Hero posts the big blind of $1.

HansVK: -- --
Hero: :As: :Jd:
Resindog: -- --
cooner: -- --
Riddler32: -- --

Pre-flop:

Resindog folds. cooner folds. Riddler32 raises to
$3.50. HansVK calls. Hero re-raises to $14.
Riddler32 folds. HansVK calls.

Flop (board: ): $31 heads up

HansVK checks. Hero bets $25

Do you think checking behind is better here?
Was my hand and/or timing (ie having been reraising him kinda frequently recently) bad for this play in general?
Any other thoughts?

It's fine if you havent been getting out of line. As you move up to stakes you're going to have to start 3-betting/squeezing so it's good you're starting to incorporate it into your game. You just need to be careful when doing it with trap hands like AJ though. With stronger hands you are obviously raising for value and weaker hands are easier to play and usually well hidden.

As played, I think you need a good reason not to bet out strong here the majority of the time. I almost always bet ~75% of the pot regardless of my hand in these situations. You'll find that people will usually fold to an aggressive follow through and if you don't do it the majority of the time you're going to have people start to play back at you more.

This is not the worst place (light 3-bet, wretched flop, loose cold caller) to peel one off, but as nuts says, you typically have to bet here.