I personally think that WHS is a little more headache than W7 or W8. My opinion is generally based on the idea of running applications on the server that aren't developed to run as a windows service. In an ideal world, I could float developers the suggestion and a donation -> poof, the service would be available. In reality, I think w7/8 give you more flexibility if these are important (explained more below)
The following can't run as a windows service last I checked
- VMware Player
WHS (and I'd assume WSE) is designed to load services on reboot and run them without need for logging in
I never found a free way to "auto-login" and "auto-start" applications in WHS. There were a couple paid ways, but I prefer the native ability W7 gives you for doing this. I really don't like completely tying the functionality of running my server the way I want to run it to a 3rd party app that may or may not be supported beyond it's initial release (personal preference)
A lot of people have said Plex doesn't need to be started in order for your library to be available, and a lot have said the opposite. In my experience, it wouldn't publish the media on the server to myplex unless I logged into WHS. Other things wouldn't work if you backed out of an RDP session unless they run as a service, so I had to use VNC instead
I have a really nice automated ubuntu VM running in VMware player, and I can leave it running in the taskbar with RBtray. This is possible in WHS as well, but not as straightforward to me. I also use WMCserver for XBMC and it feeds off of WMC being setup with channel logos, recording scheduling, tuner configuration, and guide data. This would be quite complicated to setup in WHS.
Since so many of the things I actually use just run best without WHS, I wouldn't get a ton of value from it.
Personally, I think setting up Flexraid is a little easier to do from Windows than WHS as well. Rather than dealing with editing or removing WHS default share folders and structure, you just create a Flexraid drive in windows and share it across your network. It'll run fine headless if that is your plan.
I prefer teamviewer, but any good VNC option is easier for remote management. RDP for a W7 server will leave your server backed out to the login screen unless you know a little RDP trickery. I guess it's not a big hurdle, but not as dead simple