V1: (200) UTG+1 splashy player, overvalues his holdings, I had previously seen him bet second pair first to act in a multiway pot.

V2: (150) HJ also splashy, very loose and bad aggressive player, limps in way too often, calls down extremely light.

HERO: (400) direct left of V1, young TAG, people may percive me as a lag who is card dead since when I first sat down an hour ago i 3bet my first two hands and open raised the third

OTTH

V1 limps in, I limp behind with [66], V2 raises to 12, Button, bb, V1 and I call. Pot: 60

FLOP: [6 8 9] V1 Checks, I consider betting and as I cut out $50 of my stack, I change my mind and decide to check. V2 bets 50, folds to V1 who jams, I jam next to act and V2 calls.

I considered betting OTF but i decided to check. Should I be leading into this pot to avoid it checking around and seeing a bad turn?

Yep.

5 way pot with weak stations that will call decent sized bets with a naked 8 and especially pair + SD hands? I think it's a clear donk. Like you said, so many bad turns. It kind of sucks when you get jammed on because I wouldn't expect a weak 1/2 player to jam any worse hands but you will probably be priced in at that point with these stacks. I would expect though a large percentage of the time you'll get 1-2 callers with anything from 8x no pair to top pair to FD to anything else so best to just get value here and jam brick turns.

-JP btw