possible to play with friend?
the server only matters for world verse world everything else is a megaserver. You may not always be in the same maps as your friend but if you in a party with them you can join them.
Transfering servers does cost but is free if you have no characters on your account probably best to delete characters and get on same server now just incase you wish to try wvw together in future
If you and your friend like to pvp. Then I would just wait a bit, the servers open up at random. So with a bit of patience, the server you choose will be open. However, as the previous poster said, you can do EVERYTHING, except WvW (large siege battles) together from different servers.
In my opinion its best to wait and get on the same server, as you may really enjoy WvW. However, if you are certain that fighting other player isn’t your thing, then go ahead and have your friend play on any server.
You can also transfer between servers for free by deleting all your characters.
Just make sure any items they have in their inventory are put into the bank (they’re in cities, ask in-game for directions to the nearest one) before you delete them, that way you’ll be able to use them when you recreate the character.
“Life’s a journey, not a destination.”
I go to WvW often just to get the daily there. It is quicker than doing events in a specified map. It may be that you end up wanting to go grab dailies with your friend. If you are just one day in it is better to delete your characters (put anything you’ve earned into your bank first) and switch servers at no charge.
Sorrows Furnace
Just have your friend delete his characters and move to a server that’s not full, so you can join him.