[Marwan]

I'd usually just give up in hand 1, passive players will check behind a jack on the turn when the 5 pairs.. if he limped button with an A2/A3/A4 type hand and called flop with a gut shot or bottom pair, I think he'd be glad to take showdown with A high hands against your line that looks weak... I think he can only have something like 6-7/3-6/6-8 type hands with his line that you beat, but I think a J or a 5 is more likely

Also, if I was going to C/R the river, wouldn't a min C/R be enough since he won't call with his missed draws for any amount and likely doesn't have A high? I think 88 would be the same as 72 on this board in terms of folding out hands, except you save 16 when he pushes.