They should show up just the way they were entered. So make sure every contact is the same. You would enter every contact home # first and work second (or visa versa doesn't matter). Same with email. Every contact with home email first, work second. And so on.
The point is you need to be consistent with the order you put things in if you want all contacts to show up with the same order.
Before the 2.0 update, I would use the contacts program on my mac to arrange the numbers in order. By making a template all entries follow this same order regardless of how they were entered. Than by connecting the iPhone it would load the contacts in the same order. After the 2.0 update my contacts on my computer are still in the correct order (mobile first, home second etc) but they go into the phone in a random order. By random I mean all contacts don't have the work number first, they are all in different order.
I spoke to Apple about this and they offered no help at all. I guess its not a priority to them, but to me fumbling around to find the mobile number when it used to be first because it is the most used and now its mixed in the middle of 5 or 6 numbers is frustrating and pretty annoying. I hope they fix this soon.