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Your reasoning for not betting the turn larger is flawed. If he's going to call a larger bet with all his weaker hands it will be more profitable to bet larger.
Also on the flop betting larger ($5+) seems best because he's going to peel just as light if you bet larger, therefore you get more value.
On the river, you need to be good 16.75/(16.75+33.50) = .33 or 33% of the time at least to break even on a call. Given your read that he's fairly splashy I think it's reasonable to assume he will lead the river with Ax and missed draws along with Jx, so now your job is just to put him on a range for leading, run it through stove and see where you stand. It's probably a good idea to try a few different ranges to give you a better feel for this spot in general.
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