$100 PLO on UB
My stack is $180
UTG has my easily covered.

I get [Qd][Th][Tc] in the cutoff. There are a few limpers and I raise to $4. I did this to buy the button, get some control over the hand, and build a juicy pot in case I flop my set.
Button calls, alas, and the UTG player calls as well. Pot is about $15.

Flop: [8s][7h]. UTG checks, I bet pot, button folds, UTG checks.

Turn: . Pot is $45. UTG checks. What is your move?

My problem here is that if I bet the pot, I can get checkraised for a huge amount. Even if this doesn't happen and I get called, there are too many trouble cards that might come on the river, in which case I also have to fold to a big bet. Of course, a bet might win the pot, but if UTG had odds to call my flop bet, he will also have odds to call a turn bet, especially since there is a lot of money left.

An additional consideration is that UTG is an aggressive, tricky player, who plays the situation and his opponent as much as his cards. He knows that I can lay down a decent hand.

So, I checked behind, in order to keep the pot managable.

River: . Opponent bets $25 into a $45 pot, which, can either be milking or a bluff in his case. I call and lose to 789T. (He had 2 spades.)

Questions: if there is only a bit of money left on the turn, then you should obviously not try to outguess yourself and push it in. But where do you draw the line? How deep should the money be in order for you to take the check here?
Also, what would you do if UTG would bet the pot on the turn?

Pieter