Please don't post on your phone if you can't post your hand better than this. I had to edit a bunch, and it's still missing key info like demographics of the Vs.
This is 100% a 3-bet the first time. Flatting is lighting money on fire. Why would you want to play KK 5 ways with an (approximate, since you don't give stacksizes for any V but BTN) SPR of 16.8-1? There is $50 in there with your call. Raise it up about that much more for fat value.
Your "V could call and spike an ace, or fold and I lose his action" argument is ridiculous unless V always 3-betshis BTN or had raising chips already in his hand, which would be info you need to give us. Similarly, the Ace thing is really bad results-oriented thinking. You had no idea at the time he had an ace.
AP, jam is good. Almost no one has a 3-bet/fold range at live 1/2, and in the unlikely event that he does, you probably weren't getting any more money out of him post-flop unless he hit a better hand than you anyway.
You clearly aren't thinking about poker correctly in several ways, though. Read all ofthe threads in this compendium:
https://forumserver.twoplustwo.com/3...thread-340027/