Which is better?

Villain is a 27/22/4.1 regular who 3bets 10% of the time (which is a lot). We've played higher together when I was taking shots and he knows I'm a reg in these games. He just sat down a few hands ago.

My apologies for the hand histories being a bit messed up.


Hand 1)
$1/$2 No Limit Holdem
6 players
Converted at weaktight.com

Stacks:
$200 effective.

Pre-flop: ($3, 6 players) Hero is MP
1 fold, Hero raises to $7, 2 folds, RubberDuk raises to $25, 1 fold, Hero calls $19

Flop: ($54, 2 players)
RubberDuk bets $41, Hero raises to $174,

Hand 2)
$1/$2 No Limit Holdem
6 players
Converted at weaktight.com

Stacks:
$200 effective.

Pre-flop: ($0, 6 players) Hero is MP
1 fold, Hero raises to $7, 2 folds, RubberDuk raises to $25, 1 fold, Hero calls $19

Flop: ($54, 2 players)
RubberDuk bets $41, Hero raises to $82 planning to fold to a shove,

What if the flop was ?
What if the stacks were 170bb?