Our thought process seems pretty chaotic here: on the flop we want to just call the 3bet because getting it in seems too loose, then on the turn we want to raise all the sudden given villains size, and then on the river we're unsure again.

If we have the assumption that 4betting on the flop is too loose, it means that villains 3bet range is extremely nutted. Therefore it doesn't really make sense to raise the turn. Why are we assuming that the small size is weak? His flop raise is quite small too, so why aren't we assuming weakness there?

My plan would basically be to 4bet on the flop if I thought that villains range contains enough draws/A9/A8/98 to justify getting it in with 88, or just call the 3bet and call the turn bet if I assumed that our hand was not quite strong enough to get it in right away.

I'm tilting towards 4betting the flop, just because we're up againts a weaker player (your read + villains 3bet size is not one that a good reg would use) and I think it's safe to assume that weaker players are much more likely to overplay hands that a reg wouldn't.

Once he b/c the turn, I think he either has a draw or Ax. Pot is already big on turn not to shove w/ a monster himself this deep. On the river I would shove myself or as played I would call very fast.