OK. That was quite some reading! My thoughts on this are that you seem to be the more vulnerable one in your friendship who could potentially get hurt. Just the way youve described some of his behaviour makes him appear as a bit of a player. You have a few options though:
1.) Tell him.
This could result in him saying he likes you, you like him, its all hokey pokey for a bit.
Alternatively he might say he just like syou as a friend, in which case you carry on being friends, or its awkward for a bit, but at least you tried.
2.) Dont tell him.
This will result in you stewing about it and possibly being hung up on it for quite some time. Then if one of your mates finds out it could spread around etc etc and the whole situation could get quite messy.
I dont know whether youre at school or college or uni or whatever with him, because if youl have to still see him whatever you decide to do, it could be awkward. But then awkwardness although not pleasant, not exactly life threatening.
So having thought it out, maybe you could subtley hint to him that you like him, or if he has a reputation as a player, run a mile in the other direction, and find a nicer guy.