Guild Wars 2

I just back into the game after a long break and decided to start all over. I have been looking over all the servers and I am having a hard time picking one. With the new mega servers and guild systems, does it matter anymore?

Only matters if you want to WvW with your guild/friends (in which case you will need to be on the same server).

You can always change servers again if need be in the future so don’t worry about it too much (though there is a transfer fee for that, not sure how much).

transfer fee is 500-1800 gems depending on the population of the server you want to transfer to. Sometimes they discount it to 0. Not cheap.
http://wiki.guildwars2.com/wiki/World#Transferring
But, the price is 0 if you have no characters. So if you’re just starting out, you can move all your loot to your bank, delete your character, transfer, remake your character (your character’s name is reserved for you for like 24 hours after you delete it)