So it looks like for the most part Xeon motheboard sockets are fairly standardized. If I order a new server with a Xeon proc would I be able to expect to upgrade to any processor in the Xeon family or are there exceptions to this? Do I need to stay with an L seriies if I get an L series or can I upgrade from an L to an X etc?
Nope, that's not the case sorry, there are lots of different Xeons socket (Slot 2, Socket 603, Socket 604, LGA 771, Socket M, LGA 775, LGA 1156, LGA 1336, LGA 1567 and the latest LGA 1155).
What you can do from a physical and electrical level is move between L, W, E and X variants but support for those will be entirely based on motherboard and BIOS, nothing should be assumed. There's also the TDP issue, X variants are a LOT hotter than E's which are hotter than L's too - you could easily have a massive speed boost for a few seconds/minutes - again ensure that your machine supports the specific bin you want to buy ok.
Xeons use a lot of different and incompatible sockets from one generation to the next. Additionally the server's BIOS usually only supports a handful of processors for the particular socket. I would assume that whatever optional processors are available at purchase time are basically the only options you'll ever be able to upgrade to (there are plenty of minor exceptions, "minor" being the key word).
Talk to Dell. I know that from experience there are so many variations, you'll probably end up with buyer's remorse if you go it alone. If you're upgrading Dell 2950, X5365 processor is the best you can do.