I shoved, 2 callers folded, villain calls with 88
I did not consider flat calling flop based on pot / stack sizes.
Trying not to be results-oriented:
1 - I think I could have folded flop based on my previous read that villain hasn't been out of line postflop.
Especially given that he had three callers to get through. A split pot was probably my best hope....
2 - Given the callers, stacks, reads, etc - I think preflop raise to $125-$150 would be best (I kinda feel like only raising to $100 would leave me with an unneccesarily tough decision if he 5 bet shoves?), followed by folding, with calling the worst option (though obviously not terrible).
Thank you for responses. AK is obviously a tricky hand to play when stacks are moderate-to-big, whether in or out of position....