My bane: I'm a maximizer. I sit here and think, if I'd waited just four more months, I could have gotten a faster MBP, faster AEBS, iLife 08, and 10.5 for what I paid in July. And no worries about the upgrade process...
Oh well, that's what I get for violating DaveF's Second Law Computers: "Never look at computers or prices for six months after a purchase"
And Sam's first rule of buying Mac/iPod products: "Despite the early adopter headaches it is ALWAYS preferable to buy Apple gear as close to launch date as possible" =)