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88 called BB squeeze

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88 called BB squeeze

Hi, first post. Have avoided posting any hand due to embarrassment of bad/wrong thought processes but time to get over that.

Ignition - $0.50 NL - Holdem - 7 players
Hand converted by PokerTracker 4: http://www.pokertracker.com

P1 (CO): $188.32
Hero (BTN): $49.25
P4 (SB): $33.50
P5 (BB): $49.50
P6 (UTG): $61.46
P7 (UTG+1): $57.52
P8 (MP): $51.07

P4 posts SB $0.25, P5 posts BB $0.50

Pre Flop: (pot: $0.75) Hero has 8s 8c
fold, fold, fold, fold, Hero raises to $1.50, P4 calls $1.25, P5 raises to $6.00, Hero calls $4.50, fold

Flop : ($13.50, 2 players) 5h Jd Ad
P5 checks, Hero bets $6.64, P5 calls $6.64

Turn : ($26.78, 2 players) Td
P5 checks, Hero checks

River : ($26.78, 2 players) 4s
P5 bets $36.86 and is all-in, fold

I bet the flop hoping maybe I could steal it from 99, TT, QQ, KK. Basically hands I thought he could definitely squeeze with that didn't want to see an A, didn't want to raise a bet, and might see the texture and think calling here could only get worse on a lot of turn cards. I thought I could represent a slightly weaker set of "good" hands like JJ, AQo, AJ, AT, other suited aces just betting for value, since in my reviews I noticed opponents calling my 3 bets with those hands and not wanting to 4 bet. I chose a size that I thought could get some folds without risking a ton.

When he didn't XR or fold I honestly wasn't sure what to do and I didn't want to go broke bluffing when I didn't know if he could/would fold so I just gave up.

Things I'm wondering about this hand:
Preflop should I just fold here? I can accept folding as reasonable due to not knowing how to play postflop, and not knowing anything about the BB.
On the flop do these reasons for bluffing make sense or am I attacking hands that are too strong to expect my opponent to fold to just that one half pot bluff?
Are these even the things I should be thinking about?

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