have Read the sticky, Will do my best on making this post edifying.

4 hours into session. table is 8 handed
Villain 1: Middle-aged male, very LAG today, (typically short buys and plays passively calling off rather than taking lead but has run up a stack and is being super agro)
Villain 2: Old gentleman, loose passive, incapable of folding TP, ignorant of image, position, etc.
Hero: Young, typically play fairly tight but today am playing very LAG, cbetting high %, attempted semi-bluff all-in against V1 in a decent pot earlier.

Hero has ~$1100
V1 covers
V2 ~$300

V2: UTG limps
Hero: UTG+1 KhQd - $25
V1: BB calls

Flop - Jc10h9c ($70)

V1 - $35
V2 - calls
Hero - raises $150 total
V1 - Calls
V2 - tanks a minute or two and shoves
Hero - Hollywoods and overshoves

In my mind V2 has FD and V1 has 2p, TPSD type hands, based on history and passive call of 3b.
1. What do you think of the overall line I took?
2. Should I 5b less, say $300 and shove turn?
3. Should I ever call the 4b to disguise strength?

chop it up

If you are confident of your range for V1, then I like options 2 or 3. I think your shove is blowing too many hands that you can extract value from out of the water. I think I prefer option 2. (This is assuming you have the action right. Based on what you typed at the end you are implying there was another raise somewhere.)

Because V2 tanked and called I didnt put V1 on the FD and should have raised less to entice a call, now that I look back at it though, with history (just that night) V1 after leading and calling a 3bet is rarely going to fold anything for a little more than a pot-sized shove, I really am expecting to see KQ,QJ,Q10,Q9s,Q8,87 (from v1). Before overshoving I was fairly certain V1 was coming along.

Action on flop incase it is confusing in the original post.

BB (V1) leads $45
UTG (V2) calls $45
UTG+1 (Hero) raises to $150
BB calls $150
UTG Shoves $300 total
UTG+1 Reshoves $1100 total

umm 1100 prob won't get called by v1 w/o the nuts/sets as he only has 150 invested and there's SO MUCH ACTION... i think i raise smaller but it could look stronger i guess... he's probably drawing since he called the 3b so i just bet enough to charge a draw so it makes $$ if he calls so i guess w/ a 1k pot you need to charge him 9/45*1000=200ish+implied odds so at least raise to 500-600sh IMO and be prepared to be in a bad spot if a club hits. This is really small in relation to the pot but since its multiway w/ deepstack not having as much invested its not as bad as people think IMO and could get looser calls from v1

shove any turn if flatted obviously

Hypothetically: V1 is first to act on turn. Say I 5b to $600 and he calls, Club on turn and he shoves into me.

I don't think it matters too much. Don't fold.

I think I'm inclined to just call the 300 (and commit on almost any turn) but there are plenty of cards that could scare off our action or make us second guess ourself.

If hourly rate wasn't an objective then shoving is always most +ev.

+1. Give V1 more opportunity to make a bad call with a FD or shove with a set. Making it $600 could look like an isolation move...

There are 11 clubs and 3 Jacks ott that are possible scare/bad cards. That leaves 33 cards that I am never folding to. So, I think I flatcall V2 shove to be greedy and trap V1 for more money. Otherwise, I think your 5bet line is so strong that he might even fold sets otf. But, this is the lower variance play if that is a consideration.

Don't raise UTG+1 pre with KQo...

So just open fold 200bb deep? only shortstack was V2.

raising pf with KQos is fine for a better player at a less aggresive table, but I would just say fold it if you aren't comfortable playing OOP

fwiw I raise here like 100% at the standard loose/passive tables i play at

Honestly the only time I fold here (in this game) is if I see one of the passive regs behind me looking excited about their hand.

I'm raising for value and hoping to get HU against V1. Not worried v2 is limping big because he is super ABC and never traps big hands; worst case scenario he is limping AQ.

Thanks for responses. Knowing their hands and seeing the action does anyone still think I shouldn't shove? To thinking players its like my hand is 100% face up and typically this hand would have seen a turn, but V2's AI kind of made it an awkward spot.

Ok v1 is a complete moron. I'd make it less on the flop. We have the nuts.

Hard to describe v1 but that is a fairly standard call from him. The only hand I think he considers folding is Q10,Q9 and non nut FD.

Oh and turn/river. 2d5h. Irrelavent but yum yum

OOP? Yes.