Representing a set or trips

[renodoc]

Assuming good players, deep stacks and a decent buy-in, how successful are you in taking someone off an overpair on the flop or turn with a big raise? When is this play +EV ? (what rate of success is required and is it equal to what we should expect in reality?)

For example:

$1000 buy in, 5000 starting chips 25-50
25 min into a 45 min level and villian has played 2 hands.
Hero is in SB with 44.
Player in MP makes it 150
Villian in CO makes it 400 (QQ+)
Hero calls.
MP calls.

Flop:

8 8 5

Checked to villian who bets 1000.

For academics assume MP is going to fold regardless.

Success of a push here?

What if the flop gets checked around? (this might be in violation of my original assumptions about the players)

Turn is the blank of moons and it is checked to villian again who now bets 1000. Easier to pop him now that he is obviously afraid that hero holds an 8 ???

I've read many posts where the hero is the one holding the overpair, bets on the flop and then faces a huge raise that is often interpretted as a set, and then of course is encouraged to dump it. This seems exploitable.