Good triple barrel bluffing hand, or give up?

Seems bad. Board didn't change and he called pot on the turn and you have some showdown value vs all the busted draws

It's fine at some frequency. So is xbing for SDV. It's 50/50 in theory, and an unknown straddler at this stake is as likely to be exploitable to this by defending too loose on early streets as they are to be accidentally exploiting you by being a showdown monkey.

Preflop seems too small.

You have a gutshot and overcards, but it is sort of a wet flop, and then you pot total bricks on the turn and river. If you are going to do this, I don't see the point of betting pot against fish who won't care. Plus it puts you on a narrower range. Not sure you size like that with AA/KK/AQ. However, notice villain can have almost ATC calling the small raise from the straddle.

UPDATE: He snap-called my $100 River bluff with Q3ss, paring his kicker on the end, which certainly made the call easier, but he said he was calling without it and I tend to believe him. (From his perspective, I can have all the AK/AJ/A9/KJ/KJ hands to bluff with.)

Looks pretty spewy - getting people to fold top pair at low limits when the board doesn't change is a losing proposition. I would check back this flop - overall I think at low stakes you're better off value betting lighter/bluffing less as he would probably call down even if he didn't hit 2 pr.

Just look to get paid at low stakes. Don't run triple barrel bluffs at big sizings. You can bluff sometimes if it is checked around or HU and the other player checks or makes weak looking blocking bets.

Good advice but it IS HU, villain has checked 3 times, and he's the straddle defender (against a small PFR and small flop bet).

He knows he is not supposed to have anything. There is a problem with throwing in $100 to get a fold from a 1/2 player who isn't so effected by the bet size.

When I said checked to you, I didn't mean if they check called twice as showing weakness,

I’d like to say I’m disciplined enough that my only river bluff is AK—that I’m giving up with all my AJ/KJ/K9/A9 hands that block V’s call-call-golf holdings—but I think that’s just wishful thinking, haha, I’m sure I’m spewy enough to fire $100 with all of them.

me when I have AK: great bluffing hand, I unblock all his busted straight draws!

me when I have AJ: great bluffing hand, I block all his straights!

I dont mind it but I go way bigger on flop, 15 or 20, pot OTT, you've got a lot of big QX and your main bluffs are KJ and AK imo. Unblocking TX is nice. But like others said this is low stakes and people hate folding.