Coupla hands againt weirdo 50nl.

Hand 1

This guy is weird, he's kinda laggy but open limps and 3 bets a rediculously high amount pre. His stats are 24/11/2 3bet is 27% over 180 hands. He squeezes at every opportunity. I've already 4 bet him twice to which he called one and folded the other.

Is 88+ an okay 4bet /stack off range against him?

$0.25/$0.5 No Limit Holdem
5 players
Converted at weaktight.com

Stacks:
UTG StArCuE ($46.50)
CO PohaNN ($55.60)
BTN Hero ($128.15)
SB imthesky ($62.40)
BB sinnnger ($52.00)

Pre-flop: ($0.75, 5 players) Hero is BTN :8c: :8h:
1 fold, PohaNN raises to $1.50, Hero calls $1.50, imthesky raises to $6, 1 fold, PohaNN folds, Hero raises to $17, imthesky goes all-in $62.40, Hero calls $45.40




HAND 2:

Same opp as 1st hand. Don't really understand how to play in this spot, cause I'm rarely in this situation. I think he plays kinda straight forwardish post, but very aggro. Bottom 2 against Lag/retard = get it in? I dunno. Tips and advice here much appreciated. And sorry if this is one of those simple stove moments.

$0.25/$0.5 No Limit Holdem
6 players
Converted at weaktight.com

Stacks:
UTG gigi350538 ($75.10)
UTG+1 imthesky ($61.65)
CO stopacting ($49.30)
BTN TheArtestKK ($66.95)
SB Swings_LOL ($87.55)
BB Hero ($56.55)

Pre-flop: ($0.75, 6 players) Hero is BB :ts: :5s:
1 fold, imthesky calls $0.50, 3 folds, Hero checks

Flop: :td: :5c: :js: ($1.25, 2 players)
Hero bets $1, imthesky raises to $4, Hero raises to $12, imthesky calls $8

Turn: :ks: ($25.25, 2 players)
Hero bets $14.50, imthesky goes all-in $49.15, Hero goes all-in $29.55

#1: Hmm ... TT definetively call. 99 maybe, 88 ... I don't have pokerstove here, but 88 vs a range of 44+/AQs+ would be about 45% (rough Excel calculations) I believe.
#2: The turn card is not very good as AQ/KT/KJ/Q9 now beat us, but we pic 9 more possible outs. Against a lag tard and the size of the pot any raise of a bet from us would have to be called. I think a c/push on turn is best as we would allow the lag/tard to bet/fold his air and maybe call with AK/KQ/AJ type hands.
If we are trying to induce villain to come on top on the turn, our turn bet is good as we would get good pot odds to call a shove (3-1 with our possible 13 outs). But I would bet a big more (i.e. $20) and call as our pot odds would be near 4-1.

89 is like the only hand I can see him having if he's competent .... I don't think he'd limp KQ, Q9, JJ, J5, JT, T5. I suppose Q9 is possible but much less likely. What confuses me is the fact that he flat your flop raise when it appears as if you are going with your hand, which makes me think he's on a draw, but then on the turn he decides now he's going to get it in? I think it's some really fishy kind of semi-bluff or the nuts I guess. Interested to see what others say, regardless though, you have 13 outs against the nuts.

Also, I'd likely bet/call the turn as well since your equity greatly diminishes the times he checks behind and decides not to bet his draw(s).

1) Meh its alright I guess. I would prefer if you weren't back raising though cause you're cards are pretty face up whether he knows that or not.

2) I would flat the flop. This is a limped pot on a pretty dry board. Play some poker on the turn.