Jamming with more accomplished guitarists than yourself is awesome...you learn so much...that said, jamming with a guy who has been playing two months can be good, they often have diffferent perspectives and ideas...you can learn summin from everyone you jam with, better than you or not...they will always know summin you dont.

I am not a great guitarist, but I'm not bad...doubt Im even good...but I do enjoy playing a whole lot and I love getting better.
I am a gear head, and there is no doubt that most of my equipment is better than me...I just have constant GAS, and somehow manage to come up with the cash (I save for months, then I am flat broke, but if I get a new piece of gear its all alright).

posting an ego related thread in a guitarists forum is hilarious...