Picking a bad server is akin to playing as the losing side in WoW every BG. Sure, you can keep playing and losing, but let's face it, wining is more fun and it sucks to take twice as long to get gear due to derps on your side. WvWvW will be server based, I don't think that the populations are balanced for the 500 player fight, so low pop/dead servers will be at a significant disadvantage. Couple this with the looming release of 1.0.4 in D3 and Pandamon... er MoP, there is a potential for significant population decrease soon after the game launches. Hopefully players will be right back due to WoW being WoW and everyone realizing shortly afterwards.
I play to have fun. I have also played alliance on WoW to understand that losing every time and taking twice as long to accumulate gear because your battlegroup sucks isn't much fun for myself.