Hand 1
2/5nl

Hero has ~$750 and is in bb with 78

Villain has ~$700 and is in cut-off. Villain is TAG/nitty middle-age man. He is probably small winning player. Plays mainly ABC straight forward. Skill lvl 5 out of 10.

Action:
Utg open raises to $15, Villain calls $15, Hero calls $10.

Flop TJT ($47) 3-players
Hero checks, Utg bets $20, Villain raises to $60, Hero check-raises to $130, Utg folds, Villain calls $70.

Turn 3 ($327) 2-players
Hero bets $250, Villain raises all-in to $485 total, Hero calls.

Villain tables A9

Thoughts:
-I definitely should have folded the flop. Playing a big pot on this paired board is horrendous, and I could be dead.
-I could lead this flop and the hand probably plays very differently.
-When the Villain raises the flop I'm thinking his range is something like KJ, AJ, 9T, QT, KT, AT, KcQc. I expect him to always fold his top pair hands, and continue will any decent 10.
-When he calls, I plan to play a small pot on any club 9 or higher. I'm check-folding blanks, and getting it in on small clubs.

What would you do on the flop? Is even the pre-flop call bad?

Preflop is definitely fine.
It seems pretty gross but probably folding the flop. I don't think described villain is raise/folding too much here and you're obv not in great shape against his raising range.
Turn play is fine I guess, but I don't really think he calls with worse, I mean is he stacking off with a ten here?

If you're not sure about your reads/general abilities to outplay your opponents post flop out of position, then pre should be a fold. Here you weren't able to read that the nitty middle aged man isn't raise/calling the flop and then raising the turn without a hand that beats a rather small flush on a paired board; to me this means you shouldn't be playing that speculative of a hand out of position since you are very vulnerable to reverse implied odds situations vs these opponents.

We'd have to know more about UTG to say for sure, but preflop should be a clear fold OOP.

If V is straight forward why would you check/3-bet the flop?
He is only raising with nut fds + trips.

Folding flop is best imo.

I'd fold preflop til you improve a bit with your postflop skills. Then squeeze unless UTG has a ridiculously tight opening range.

FWIW I agree you really butchered this hand post flop. I do understand that you believed you could win a big pot from trip Ts.

With no reads on UTG, I think this is a fold pre.

When the nitty player raises, I think this is a fold as you aren't closing the action