[Man of Means]

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Should I not raise the flop? I did so to make it heads up against villain and to make him pay as much as possible (how could I know I would chicken away from this plan on the turn).

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I think if your read says villain will go down in flames with a weaker hand, then raise the flop with the intent (PLAN!) to get it all-in on the turn. If the stack size prevents this from possibly happening then you may choose to call the flop and either raise the turn if it looks good or "chicken out" (by way of a fold or pot control).

The thing about betting small on the turn is that is actually more bold and risky than pushing. While it may be easier for him to call smaller amounts twice with a 10, you are giving him a better price to get the pot AND your remaining stack.