I like your choice...I think I would like the extra sear burner, though personally I don't use the side burner much.
Found myself also being hesitant spending that much on a new grill. Around here (Northern VA) there is a constant flow of used webers on craiglist etc. Eventually found a 2 year old genesis II for $275. But I see the older ones for even cheaper. Trick is finding them where the body is in great shape as you can easily replace grates/bars etc. Surprised there is not a similar market up there. Around here if someone asks for $350/$400 it might hang around a bit but down at $300 or less they just go.