Button seems like a good player. Lost half of a nice stack tying to get fancy here. Should I have played this hand differently? As played do we call his river bet?

Preflop is fine and probably ideal vs someone opening a wide range. The flop gets interesting - I might consider checking as this is a great hand to add to our checking range, and also he rarely connects with this board so you're hoping he stabs at it and continues on future streets. So he calls the flop bet and we get to the turn - I think he gets here with some Ax/Kx or maybe backdoor heart floats along with pairs. I might consider checking as it looks like we stabbed with a bluff and are giving up, and a big portion of his range are worse hands that will bluff. On the river you'd expect him to check back his mid pairs, potentially Ax that called the turn, so his range is very odd. 4x,TT,22,33,hearts - the backdoor hearts might contain Ax that might check river anyways so very limited on the hearts. Very marginal spot - I think I call but you'll lose a fair amount

ProPokerTools Hold'em Simulation

166 trials (Exhaustive)

board: T4455

Hand	Pot equity	Wins	Ties
Ts7s	38.55%	64	0
22,33,Ahx,TT,4x,Khx	61.45%	102	0

I love this. I think pre the 3b is fine, if we do choose that line, I'm with this poster, I think a check on flop makes a ton of sense. Also just calling pre and check/calling down seems a fair line here too. As played, I think I prefer check/calling river over check/folding and think bet/folding river is intriguing as well.