I played this hand last week at a home game. SB is an odd player, he can be very agressive at weird times and very passive other times, he is by no means a winning player in this game, he plays occasionally usually dontates a couple hundred and doesnt come back for a while. Button is another donator, I already stacked him one with a set vs his flush draw.
SB $350
Button $120
Hero covers both

I get Jh 9h on the CO and raise to $6 after 4 people limp this is my standard raise tButton calls so does SB. Flop is . Checks to me I bet $15. Button mins to $30. SB calls. I call to try to peel one off. Turn check to me, I check, button checks behind. River , giving me the nut straight. Sb bets out $20, I raise to $50. Button pushs for $75 total. Comes back to SB who thinks for a long time and just calls. I am obviously not folding for $25 more but can I reraise this river and try to build a side pot against the SB?

Is the question whether you can raise the river (is it allowed?) or whether you should raise the river?

In order: I say no, and yes.

Thats pretty funny I totally missed the fact that I couldnt reraise because of the bet sizes so did the rest of the table. We have a long discussion after the hand about if I should have raised or not. The general concensious was that I should have overpushed which I absolutely hate, SB is not a great poker player but also not a total donkey I cant see him calling an all in with a non FH ten.

At the time I was just happy to win the hand and win a decent sized pot but after thinking about it for a while and talking to Devbert about it I think I left value on the table, I think with the size of the pot I should have raised $50- $75 on top and SB would have been forced to call based on the size of the pot. He is not good enough to smooth call there hoping I would reraise. I thought there was a decnet chance with his turn check that the button had a monster it turns out he was a donk slowplaying trips. Button showed K10, SB showed T3 and I won the pot.