[Mitke]

1.
Betting out might clear some A outs from A9/AT, just maybe. K-outs we probably cannot clear as KQ isn't folding ever and KT/K9 have a gutshot. There's RIO on offer for our A/K outs. If our image is a LAGTAG and the villains are paying attention folds aren't as likely if you image was tighter.

It is pretty unlikely we have the best hand or equity edge here (somebody could stove this please) as that flop hits a lot of limping hands and hard. We are very unlikely to get a free card on turn with three villains still left to act behind us - even if they are passive.

I don't like the bet. Check and re-evaluate based on odds. Go aggro when you have a hand vs LP-donks.

Outs, J outs are obviously good and might offer good implied odds from donks having a K. However, I doubt all four Jacks are still in the deck. A and K outs are heavily tainted. 5-6 outs is my guess.
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2.
It's a small pot, we probably aren't in the lead after BB donks and we are possibly pushing out SB with a worse hand than ours. However, raising for free card has its merits here vs. these passive villains.

I give Jacks 3.5 outs, overcards 2.5 (reverse domination, straights) + 1 for BDFD. 7 outs.