Separate Checks: Is it really THAT big of a deal?

I understand that asking for separate checks from a restaurant/server's standpoint is probably a pain in the ass.  However, in this day of computers, shouldn't that be an easy task?  We, as patrons, know the paying out process will take longer and we don't care, but is it really that difficult to separate checks and get the checks right?  Maybe it is.

Then, there's the issue of one person paying the whole bill (sometimes for a bunch of people he barely knows) who then has a huge debit on his credit card and a pocket full of cash from being reimbursed that he didn't really want to be carrying around the rest of the night.

Especially in a tourist town (hello, New Orleans), separate checks shouldn't be that big of a deal?  Right?  Maybe I'm a peasant and don't understand how the rich people do things, but us normal people would like to not be treated like we're asking too much of the world by requesting separate checks.