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1) Anyone raise this flop on either opportunity based on the action?

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I like your line. There certainly is an argument for simply pushing here and you may end up in an all-in coup anyway with the orginal bettor still to act, but this way allows you to fold if an open pair hits on the turn. If Villian 1 does raise it up, you certainly have enough equity to go along for the ride.

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2) What do you think of Villain 1's play of this hand?

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I dont like it at all. One of his opponents is clearly drawing and he likely has the other one dominated. The rainbow flop is a good thing, but the 9-10 hit a lot of decent drawing hands. The problem is that he won't really know which outs he has to dodge. He holds 2 potential blocking outs, so if he is going to raise he should have shoved his entire stack in. This way, he may force the drawer to drop if the drawer is the big stack. Why force yourself into making a tough decision on the turn when any card from 6 to K that doesn't pair the board is a possible worry.