I can offer a few thoughts for what they are worth.

Hand 1 If he's a calling station then betting with a hand that can showdown seems ok but when he wakes up and starts betting I think you should give him credit for a hand. It's ok to fold even having made several bets.

Hand 2 You tried to move him off his missed overs and he announced a big pair. I wonder if calling and betting the turn if he checks might be a better play. Interested in what others think.

Hand 3 I guess 2nd barrels can be read dependent, I'm not very good at choosing the right times. Here though has he called you with a gutshot? Any other hand is beating you. I'd check the turn and fold to any big bet on the river.

Hand 4 Shortstacks vary a lot but still if he's reraising you I'd put him on a bigger pair or a fairly strong ace. So you will either be a very slight favourite or a big dog. Shortstacks profit when big stacks play too loosely against them, you need card strength to take them on. I'd fold

Hand 5 is bad luck

Hand 6 I think you call pf of his 3 bet is marginal at best. You are calling $7.5 to win $80 so you need to stack him every time you hit to profit. As we see even when you get it all in sometimes you get unlucky.

Hope some of that helped