I feel dumb when I lose hands like these. Is the turn raise ok, trying to build the pot with a draw? Is the river bet stupid? In retrospect I feel like I should bet it harder or not at all.

Villain is very tight, 11/2/2.5 over about 100 hands, but I don't have any specific reads. My image is probably slightly laggy.

Party Poker No-Limit Hold'em, $0.50 BB (9 handed) Hand History Converter Tool from FlopTurnRiver.com (Format: FlopTurnRiver)

SB ($47.75)
BB ($97.25)
UTG ($23.25)
UTG+1 ($64.73)
Hero ($52.55)
MP2 ($64.43)
MP3 ($23.55)
CO ($65.54)
Button ($17)

Preflop: Hero is MP1 with T, 9. SB posts a blind of $0.25.
2 folds, Hero calls $0.50, MP2 calls $0.50, 1 fold, CO calls $0.50, 1 fold, SB (poster) completes, BB checks.

Flop: ($2.50) 5, 3, J (5 players)
SB checks, BB checks, Hero checks, MP2 checks, CO checks.

Turn: ($2.50) 8 (5 players)
SB bets $1, BB folds, Hero raises to $3.5, MP2 folds, CO folds, SB calls $2.50.

River: ($9.50) 4 (2 players)
SB checks, Hero bets $5, SB calls $5.

Final Pot: $19.50