OK, I know you're mainly talking about windows but...
I used to develop on windows for deployment on *nix servers. Sure there were lots of gotchas with this way of working, but you just kind of get used to it.
In October 2005 I switched to Linux, initially as an experiment, but I never went back. There was a steep learning curve. I thought I knew *nix pretty well after 10 years of dealing with it, but I knew nothing compared with the amount I learned using it on my desktop machine.
Workflow has been so much smoother developing and deploying to similar platforms.
More recently, we have even started to pick servers running Ubuntu server, so that they most closely match our Ubuntu desktop development machines.
If you are talking about the difference between a desktop and a server edition, I'd guess you needn't worry about it. If you're developing on one OS for deployment on another, I'd consider changing your desktop platform.