Live tourney about the 3rd hand in Villain 1 has just taken a pretty big pot by calling down someone in position with TP medium kicker vs. top pair worse kicker.
Villain 1 also likes to make bad calls with two overs on the flop, and rarely bets out multi way first to act with less than a flush draw and an over.
And likes to see flops with connectors suited and unsuited, suited Aces, and small pairs.
I have also seen her open limp JJ before.

Villain 2 will reraise pre with anywhere from 1010+ and AQs+ but I have seen him open limp AA before a previous day.

No Limit Hold'em Tournament - t50/t100 Blinds - 8 players

UTG: t3020
Villain 1 (UTG+1): t5200
MP1: t3000
Hero: t3350
Villain2: t4200
BTN: t3100
SB: t2200
BB: t3500

Pre Flop: (t150) Hero is MP1 with AK
1 fold, Villain 1 calls 50, 1 fold, Hero raises to t250, Villain 2 raises to t600, 3 folds, Villain 1 calls for 550

Hero? (Hero flat calls t350 more)

Flop: (t1950) K 9 6 (3 players)
Villain 1 checks, Hero checks (if Villain 2 has an underpair to the K he is checking this flop alot and the board isn't overly scary to me but I suck so....), Villain 2 checks)

Turn: (t1950) Q (3 players)
Villain 1 bets t300

Villain 1 would do this with a Q (QJ, AQ, KQ) or even A9 given the lack of strength shown.

Bet the flop since there was so much in the pot already relative to my stack size and there are very few hands in Villain 2's pre range I'm behind?

dude bet flop for sure... unless you were going for a c/r, but that looks too strong imo. I like leading for about 2/3 the pot here. this is live, don't give too much credit to your opponents, esp at a $20 live buy-in...

Bet 1/2 to 2/3 pot on the flop leaving you with about 1500 for a turn push if there are still players in and you did not get heat.

As played, I'm raising to 1000 thinking that I am ahead of most ranges for these two villians. It is tougher to play now that V1 got a free card and may be very good or just think you are all very weak.

The only hand that you put him on that is beating you is KQ........Easy raise to 1000-1200.

As played I raised the flop to 1500, Villain 2 folds, Villain 1 insta flats saying I call.
That is not good.

River: (t4950) K 9 6 Q 9
Villain 1 checks, Hero checks behind

I checked on a feeling that I'm behind here to a likely KQ, and Villain 1 is never ever folding two pair on the river or even top pair, she is that bad.
If it's QJ she probably gets away from it so in my mind I've got nothing to gain unless she has something crazy like KJ she will call with that she played totally different than I have ever seen her play before.

Villain turns over JTo for the straight on the turn.

After the hand was over I was kicking myself for being overly cautious and not betting the flop.

meh, leading into a 3 bettor is donkish

i wouldnt sweat it, just be happy that someone is going to limp call a raise and 3 bet with JTo and get those chips back

also, raising the turn is pretty bad, imo

also, anyone telling you to lead into the 3 bettor on the flop with AK here is misreading the hand i would have to assume.

Jam pre.

Before you posted results, I was going to say this is obviously JT because low-end live players love JT and will play it under any circumstances, especially women. Areaman, you are speaking from an online perspective. Live players at the low buy-ins tend to be passive calling stations, so you DO want to bet your TPTK here precisely because all sorts of garbage will call you down and pay off; if he has AA tough luck and you go play cash.

brad nailed it...with your stack just jam pre...failing that bet call flop

That too given your read re his range, etc, etc.

a) im a live donk
b) leading into a 3 bettor, typically sucks for a ton of reasons and if you really want me to list them i will
c) i didnt really look at stacks, but yah, ship or fold pre depending on read of 3 bettor, but for most live players id have to assume their range is JJ+ and AK after your iso raise of the limp but i think its typically ship

that board on the turn, raising..sucks, ducy? will explain if neccesary.

I see Y, but perhaps you were talking to OP. Like I said earlier, when a passive woman playing live leads that turn, I can probably find a fold there because I would put her precisely on JT. I completely disagree with you re betting flop in a $20 live - the 3-bettor will check behind with QQ/JJ/TT always but he will pay you off if you just bet it. I just find live play too passive to check there - I think you lose too much value, but I am very interested in hearing your views to the contrary.

As played, jam the flop. Seriously checking tptk on a drawish board with psb left?

sorry, some of those comments werent directed towards you.
they were general comments.

anyways, tehre were a lot of mistakes made here by op, so many you could point at any street and yell MISTAKE...

either way, ship pre.