Am I Playing These Wrong???

[HighStakesPro]

Not only did he call a raise with 53o, but he didn't raise you on the turn when it was probable that he had you beat. Remember that he probably would have called you down if the flop had been 863, and he will make other unprofitable types of plays as well. If your opponent is typical, he will fold garbage like 53o and obviously many other hands as well. A typical opponent might call with A3s on the button, but probably would not raise if you bet on the flop. Even if he would, this is the only possible hand that he would play that way, while there are many ways that he could have top pair or some straight draw including a seven, or even 99/TT. On balance you will wil a lot more by betting than just check/calling. If the river was an 8, that would make checking a much more reasonable choice, since he is likely to have top pair, although it is not out of the question to bet anyway.