HAND #1
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I think I check here at the turn. My thought is that if he called my $4 bet on the flop he could easily be chasing and with a flush draw and a straight draw on the board that possibility is most likely to me. His call could mean he figures me for the same. I think I check here and try for the free card. Then if another diamond falls I would probably lead out with a 1/2 pot bet and take my chances with my Q-hi flush. If no diamond falls then I am faced with my only option being a stone cold bluff. I would check the river and fold to any bet from Player8.

HAND #2
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Based on your description of his style of play, I think I put him all-in here. I would take my chances that he doesn't have the flush here based on your notes on him.