Unless you've seen Villian calling a lot of overbets, I don't like either push. My experience is some loose players can find a fold if faced with a large bet. In the first hand, if Villian has a flush you're probably going to get the money in anyway, but might scare away a worse hand with an all-in (players like this might not think much about the three clubs until you make this massive bet). I'd just raise it to $15-20 and hope Villian comes over the top.

On the second hand, I'd raise on the flop. I think the turn bet allows the Villian to get away from a lot of hands you beat. I think a lot of this depends on your read of Villian. Is he making a lot of bets himself, or is he just calling bets down?

In general, I like making lots of 2/3 pot to pot sized bets against loose-passive players rather than all-ins. No reason to give him a reason to fold his top pair weak kicker.