Windows Home Server (WHS) has a lot of promise, offering an easy way to get things like backups, shares, a website and remote access. I think the biggest problem with WHS is that it's targeting a market that's already figured out how to do most of those things.
With the expiration date looming (12/15) and a $180 price tag to keep it up; I've started planning my migration off of WHS. Weighing the price against what other things I could get for the money (750GB HD), I just can't justify the price tag for an OEM (non-transferable) license.
Running through the features there's really only one thing (backups) that I'm really going to miss when I turn off the WHS box.
Shares - This is easier with WHS, but it's not that hard to setup in the first place. Simplifying the process adds value if you don't know how to share a folder, but I think most of buyers for WHS already know how to do this. If they don't, there are plenty of guides on the internet, and anyone who knows that WHS exists knows how to search the internet.
Remote Access - This is much easier with WHS, but (and maybe this is just my experience) it's also much slower. Personally I setup RDP tunneling over SSH a long time ago, so this feature didn't net me anything functionally. It was more convenient to not need a SSH client installed on the machine, but it was so much slower than the alternative, any convenience was far out weighed.
Website - Another thing that's easier to use, but very limited. With so many free website applications (Community Server being one) that offer so much more functionality I never spent much time looking into this. I have to admit some bias with this one; in real life I spend most of my time working with web applications so I found the configuration to be limiting, especially when it came to using an alternate (non-live) dns name. There really should be a feature to enter a dns name and have WHS generate a new cert based on that name. The files section is nice, especially the automatic zipping, but not a huge leap over ftp (or a secure alternative).
Unified Storage - This is a really neat concept, but I found the implementation to be annoying. Copying large files, or multiple large files, went much slower than it should have because at some arbitrary point demigrator would kick in and kill disc I/O. Trying to copy a set of large files from one PC to the WHS and a set of large files to a different PC was painful. I ended up splitting the available disc into two groups, one for WHS to use for backups and misc files, the other a JBOD collection that I managed like normal disc.
Media Connect - I have no use for this feature. I don't say that because I don't think it's valuable, I just don't have any need for it.
Backups - I will miss this one, kind of... It's really nice to be able to easily automate backups, I wish there was more granular control over what gets backed up, but it's nice. I'm going to blame the pre-Gold nature of my installation, but I found this feature to be no where near as reliable as it needs to be. I had around a 50% success rate for retrieving files from backups (only tried it 4 times). My backup database got corrupt twice, and I had to delete the entire backup set to fix it. The backup service fails periodically and I have to reboot the box to get it going, but the there's no status message to tell me that it failed. I find out when the connector application complains that X computer hasn't been backed up in 5 days. Again this is probably pre-Gold teething, but it doesn't fill me with confidence.
Mail - NM, this isn't a feature of WHS;) Where is the POP service? SMTP is installable, but that's not terribly useful by itself. I'm not looking for a full-blown Exchange install (wait wasn't WHS based on SBS, which has Exchange?), just something simple that I can enable mail if I want to.
Maybe v2 will offer better value for the $$$.