How far do I take blind stealing?

[Eeegah]

BB is a SLAP with about 2.5+ AF and around 27%VPIP.

PokerStars 0.25/0.50 Hold'em (10 handed) converter

Preflop: Hero is Button with T[img]/images/graemlins/club.gif[/img], 9[img]/images/graemlins/club.gif[/img].
<font color="#666666">7 folds</font>, <font color="#CC3333">Hero raises</font>, <font color="#666666">1 fold</font>, BB calls.

Flop: (4.40 SB) A[img]/images/graemlins/diamond.gif[/img], 2[img]/images/graemlins/diamond.gif[/img], Q[img]/images/graemlins/diamond.gif[/img] <font color="#0000FF">(2 players)</font>
BB checks, Hero...

I realize that if my steal is called then high-card strength is much more important than being a suited connector. Should I have just chucked this preflop?

The flop hits, and obviously it sucks hardcore for me. Yet he checks, and I'm left wondering if I can represent a monster (easy to do with this board) and get him to fold, or is he about to checkraise me. I don't know if the villain is capable of such, but .25/.50 checkraising is rather uncommon and I lean strongly towards "no" unless proven otherwise. If I check, I'm guaranteed to be bet into on the turn and I'll have to let it go. Is it worth a bet to knock him off?

If possible I'd like to make a bit more general discussion, however. Unless I missed it, SSHE is strangely silent when it comes to blind steals and defense (perhaps since SS games are loose enough to make it kindof rare), so I'm basically left with raising the upper range of what I'd limp with, otherwise folding. Conversely, I have no idea what I should be defending blinds with, but I suspect it's either raise or fold. Any pointers?