Probably wait until itemization patch. Both Diablo 2 and 3 are supposed to be played once in a while, go back when you're bored.
1. spend real money to get the best gear so you have like 1,000,000 damage.
2. you've just beat diablo 3.
3. pat yourself on the back.
Playing with people can make it more fun. My problem is I'm picky about who I play with and the game doesn't lend itself to social interaction within the game, so you're limited as to where you can find people.