I run into these type of situations a lot and I generally don't know what to do a lot of the time. Wanna get opinions on my thought process with a few examples. These questions are generic and part of the answer is probably villain specific so lets assume its 100bb deep playing 2/5 and villains are unknown fish.

Example 1

I three bet an unknown fish with JJ in position. He calls and flop is A66 rainbow or flush draw doesn't effect my question....He checks.

Reasons to bet - Get value from worse hands (smaller pp's, Flush draws, protection vs hands that missed but have over card equity.

Reasons to check - Tough to get value from worse and checking might induce villain to bluff turn and maybe river. Problem I run into is that if I check I always feel like I'm obligated to call turn and river due to showing weakness on flop.

Example 2

I open 9c9d get called by button and bb. Flop is J 7 3......

I bet flop and button calls. Most turns I really don't know where I am at or how to proceed. Should I be checking this flop? Seems like I can get value from worse and also protect vs hands with equity. Help please lol

i think you can get away with betting really small

On the A66 flop, cbetting is villain dependent for me. If V is loose with a wide range, I'll cbet. If he's tight, I'll check. The other thing I like to do in these flops (whether I 3bet or just PFR) is check back Ax. It protects my check back range and induces bluffs or calls from worse.

Cbetting 99 on J73 seems fine. Not sure why you don't know where you're at once BN calls.

Hand 1: C-bet most of the time. Just check behind occasionally and favor villain that seem passive. Against passive villains you can fold because they check down anything you beat. In this hand you can c-bet smaller then usual, as the hands you beat will fear being sucked in and the board is drawless.

Hand 2: C-bet more often then not but with two unknown opponents something around 60% of the time seems right. If you get just one call plan to barrel turn some of the time but less then 50%. On this board with two opponents you need to c-bet the usual size because there are a number of middle hands that will call a small bet to see if their hand improves or you give up.

Hand 1 is easy check back. We can hardly ever have 2streets value from worse pair so why should we care about value otf. The same with FD, our hand is too weak for 2 valuebets, betting flop does not take more value just because we dont have turn valuebet. Ofc there may be some tiny difs based on suit of your JJ and whether A on flop is the FD suit. But basically we do not play 2nd pair bet for value esp not against strong range.

2nd hand is better cbet flop, this time rather for protection against overcards. When called we usually aim to get to cheap SD.

Of course all this is player specific... but let's pretend we're completely uninformed about opps.

On the JJ with the A66 flop IP.... If you give V a typical calling range (top 15% x AK, AA, KK).... you are about 58/42 ahead OTF. You drop 25% equity of a K or Q turns. So in general - I'm cbetting - one and done.

On the 99 with the J73, again with no reads against the 1 caller. Their range probably includes a few Jx (AJ, KJ, QJ, JT)... some 7x, and a few gutshots probably. You aren't likely to like any turns (exc 9). I'd be check/folding mostly. I might barrel an AK occasionally.