If you're into World of Warcraft and embrace that style of MMO, being good at it can provide you quite an experience and community involvement. Due to the scale of the community, it has quite a bit to offer.
Well, the most rewarding would be a game/genera that has real rewards. Either teaches a real skill (i.e. Rocksmith teaching guitar/bass), or has actual cash prizes like games that have a professional circuit.
Probably fighting game or RTS for me, I got really good at WC3 back in the day and some of the higher ranked 2v2 matches I played were incredibly satisfying to win.
Also I find it pretty rewarding to actually finish a game nowadays as weird as that sounds. I have such a huge backlog and spend most of my gaming time online that I rarely finish single player games anymore but when I do it feels pretty good.
Also maybe spelunky or supermeatboy since theyre both so challenging. I know its not a video game, but I think being really good at chess would be fun.
I still remember all the times I played it and got further only to then not get as far the next time. Finally finishing it was a really rewarding experience for 9 year old me.
Of todays games... ARMA 3 MP is pretty rewarding to be good at.
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