Awesome discussion so far, thanks guys. Before I give my thoughts on the flop, I just want to preface it with this: I'm not claiming to "know" any answers either (hence why I posted); I just happen to be the guy who played the hand, so think of me as a witness rather than an expert.
Anyways, IMO, I don't like raising flop here primarily because I think it lets V1 make the best possible decision with most/all of his flop donking range. Some random 8x/99 hand? He gets to muck (and no more value for me); I don't think he would ever really consider continuing with those hands, even though he knows I have semibluffs in my flop raising range, given that: (1) we're deep, (2) I have position on him, and (3) V2 is in the hand. A nice, nutted combo draw like A5dd? He's free to 3bet and put me in a tough spot with my pretty obvious overpair (I can't really have 22/33/32, so my only nutted hand is 88). How confident was I in my bet-sizing read that his flop bet was rarely sets/2pair? In hindsight, I think it's pretty reliable. In the moment and at the table? I wasn't so sure...
Put another way, even if V1 doesn't reraise us, V2 can and most likely will just jam it in with Axdd/Kxdd/54dd type hands (remember she's tilty and losing, so if she see's like $200 from both me and V1 already in the pot, she's gonna think, "sweet pot odds!"), if that's what she happens to have. And then we're kind of stuck, right? Basically, I didn't see any real, clear extra value to be gained by raising the flop, but I could foresee a bunch of marginal/thin scenarios that would be generated by me raising.
I dunno how to put this scientifically, but in my mind, flatting gave me the best chance to keep making better decisions than my opponents. Raising just seemed too gamboooollll-y (in the sense that I'm just hoping/praying for my opponents to not be nutted, or for them to make suboptimal decisions like continuing with bad draws or not repopping with combo draws).
So, to recap and continue:
Flop: 8
3
2
, pot $130.
V1 leads for $65. V2 calls. Hero thinks for about 10-15 sec, and calls.
Turn: 8
3
2
2
, pot $325.
V1 leads again, same timing as flop (like 2-3 seconds), for $150. V2 tanks for a bit and folds. Hero ??? For the record, we have ~$1100 effective stacks still.