I couldn't get my normal converter to work with stud so bear with me.

6 players (antes $.10 apiece, pot 60 cents)
Dealt to me: ([Ac][As])[9d]
Player 2:
Player 3:
Player 4:
Player 5:
Player 6:

Player 5 brings it in for $.15.
Player 6 calls.
I complete to $.25.
Player 2 calls.
Player 3 folds.
Player 4 calls.
Player 5 calls.
Player 6 calls.
Pot: $1.85

Me: ([Ac][As])[9d][Ad]
Player 2: [5c]
Player 4: [7d]
Player 5: [9h]
Player 6: [Jh]

I bet $.25. Only player 5 folds, everyone else calls.
Pot: $2.85

Me: ([Ac][As])[9d][Ad][6c]
Player 2: [5c][5s]
Player 4: [7d][Kc]
Player 6: [Jh][Jc]

Player 6 checks.
I check.
Player 2 bets $.50.
Player 4 goes all-in for last $.45.
Player 6 calls.
I CR to $1.
Both Players 2 and 4 call.
Pot: $6.30

Me: ([Ac][As])[9d][Ad][6c][Ts]
Player 2: [5c][5s][3d]
Player 4: [7d][Kc][7s]
Player 6: [Jh][Jc][8h]

Player 6 checks. I bet $.50. Players 2 and 6 call.
Pot: $7.80

Me: ([Ac][As])[9d][Ad][6c][Ts][4s]

Player 6 checks. I bet $.50. Player 2 reraises to $1. Player 6 folds. I reraise to $1.50. Player 2 reraises to $2 and is all in. I call.

So I guess my question is, how was my play on 7th? Should I keep reraising as much as possible with trips in this situation or should I have just checked/called when a boat didn't hit? I was 50/50 at the time on which option to take, and still am very unsure of what I'd do if a similar situation happens again, so I thought I'd pick your brains to see if you can lead me in the right direction next time.

BTW, I know my check on 5th sticks out a little bit, but player 2 had been very aggressive whenever he hit any sort of open pair (he just caught 5s) and I was fairly certain I'd get a check raise in there. He didn't disappoint.

Given what your board is showing, player 2 could well be under the impression his trip 5s or two pair 5s and jacks or something is good, especially given he's short which could indicate a poor or tilting player. I think there's enough of a chance of that to make putting in 2 more BBs profitable. If he raises again and has more money behind (and it's not a site that caps on 7th) you should then just call. If his board is more threatening to trip aces you need to be more cautious but here I think raising is fair enough.

Thanks for the response Monk. I think what ultimately made my decision to raise was just as you mentioned; that he had no idea he was going up again trip aces and thought trip fives could be good. If he put me on two pair his play made sense.

Turned out I managed to lose the entire pot in this episode. The first all-in player (player 4) caught a seven on the river to make a full house (sevens over kings), winning the main pot and player 2 did indeed catch a full house on the river (a smaller one; fives over sixes) to win the side pot. Seems like everyone in that hand got lucky except for me. That's alright though. I caught a straight flush today to make up for the entire hand.

It's a pain when people run you down like that. Just remember to keep betting your strong hands very aggressively to make them pay on the occasions they don't!