V: Young Asian woman, loose, limp calls often, capable of getting aggressive postflop, likes overbets. Seen her make moves like donk overbetting TPGK into 5 people. Seen her play hands like Q9o from EP.

H: Young white man, probably has nitty/weak image. Only hands I've shown at showdown this session are A8s and JJ. 300 behind, V covers.

Folds to H in MP who makes it 15 with QhQs. CO, BTN, and SB (V) call. Flop is 2c8c5s. V donk bets 10.

Not sure what to make of this bet. I think her range includes all 22-99, all broadway clubs, all AcXc, 67, 89, and maybe some Q8+. Maybe 58s? I don't think she has complete air here since donking 10 into 60 with 3 left to act isn't going to get too many folds.

Obviously never folding here, but not exactly sure how to proceed. I think I want to raise to either take it down here or get heads up with V. What kind of sizing should I use for a raise? Is there any argument for just flatting? Thanks.

Are the other opponents fishy/loose? The more they are, the higher your raise should be if you want to be HU with villain.
On the other hand, if you let the pot grow too much, you coul easily play for stacks against someone who plays (in my opinion) 70% of hands on the SB. If you are willing to do that, it's fine, enlarge the post and let her bluff out of position ( does she bluff?)

This type of bet is generally a weak FD or a monster given the villain description. Just make the normal bet you would have made. She's likely to call no matter what.

Stack sizing makes a difference going forward as to how to play this.

CO and BTN are both a bit loose pre, but seem to be fit or fold post.

I haven't seen her bluff with total air, but I think she's usually betting with any pair or a draw. I've only been at the table about an hour though, so it's possible she does and I haven't seen it yet.

I think I'm okay with playing for stacks here since I think KK+ would've 3-bet pre and I think a set would've bet larger on the flop or tried to check-raise. What size would you use to enlarge the pot?

I started the hand with 300, V covered with ~550.

I think my normal bet would've been some where around 40. This flop is pretty dry so I don't want to bet too big (maybe bet 20 heads up?), but I also don't think I want all 3 players to call and play a bloated pot MW. Thoughts on that?

1/6 pot bet looks like a bet Villain wants to buy a third club with ( as both you and venice10 hinted). I would punish her with a 4x raise. 40 seems to be a good tradeoff between excluding the other players and having room enough for playing even of you receive another call

40 is a good size. You don't want to bloat the pot. On the turn, another 1/2 pot bet on the turn if the villain does another small donk bet. Proceed with caution if the villain bets big or raises big on the turn.

Thanks. I did end up making it 40. CO and BTN fold, V calls. Turn is 3d. V bets 95 into 100 pretty quickly. The stack sizes make me think this is a jam or fold situation, since a call only leaves me with a 1/2 PSB OTR. (Am I right to think that?)

Not completely sure on this read, but I think she would've 3-bet a set OTF. If that's true, I'm having a hard time ranging her here. The TPGK donk overbet from earlier makes me think this could be 99-JJ or maybe an 8 with an overcard. She might be getting aggressive with a big draw to capitalize on my nitty image. I forgot to include the double gutter in my earlier range for her, but 46 and A4 get there. However, I think we can discount A4 given the flop call. H?

I think it's time for shoving. Villain could also be semi-bluffing her draws and giving her another card is the last thing we want. Sometimes she will snap call with a set (we're dead), two pair ( we could win if board pairs OTR), worse overpair or A8/K8 (good) but most of times she will muck the bluff/the draw and we will win a good pot on the turn.

If villain was tight I would be way more cautious but this is not the case in my opinion