Let me first provide a little background: I've been running Linux (mostly Red Hat, then Fedora) at work since 2002. The latest distro that I ran on my Dell D420 was Fedora 9, running GNOME. I'm a manager, so pretty much all I used was Firefox for web, Evolution for email, OpenOffice for writing and editing documents. (Although, I'd recently been using our work webmail system to read my email on the web - more convenient when I'm away from the office.)
Since I also work on a personal web site in my spare time, I made regular use of the GIMP (for updating the graphics) and Terminal so I could ssh into the web server.
Hardware: I'm plugged into a standard Dell D-series mini-dock, which provides me with optical media (CD-R, DVD) which is presented to the system as a USB optical drive. There's also a handy set of USB ports, which I have connected to my Dell 1280x1024 monitor. The monitor has USB ports on the side, which are easier to reach if you want to plug in a USB memory stick, and is also where I connect my USB keyboard and mouse.
On Thursday, January 15, the desktop support guys dropped off my "new" D430 laptop with the standard Windows image. The CPU is a little faster than the D420, but otherwise it has the same memory, wireless, etc.
From the start, it was a hassle. Where Linux easily recognized the mini-dock as a USB hub that happened to have an optical drive attached to it, Windows did not. After 15 minutes of messing with it, and a reboot, we finally managed to convince Windows that the dock existed. So now I had an optical drive. More importantly, I could use my external USB mouse and keyboard, rather than leaning way over to type on the laptop while it was still in the dock.
Next, we fought with Windows to get it to recognize my 1280x1024 external monitor, which Windows was convinced was 1024x768. The support guy recommended rebooting with the laptop lid closed, thinking that Windows didn't like driving two displays at different resolutions - we tried that, but rebooting didn't fix the problem. The support guy suggested the problem was with the mini-dock, but I didn't buy it. Eventually, we figured it out (I don't remember what he did) but it required yet another reboot for the resolution to show up properly as 1280x1024 on my external monitor.
For those of you keeping track at home, that's 3 reboots to get basic functionality working on my laptop. Not a great first experience with Windows. I'm off to a great start.