Just an update of my experiences after I moved my email, calender, notes etc. into Windows Live.
All in all - I am very happy with it, works fine and it is a big relief no having to look after my own server.
I used the "public folders" of Exchange quite extensively in order to store short notes or some miscellaneous pieces of information. I moved that over to OneNote - works great and is highly recommended!
A couple of days ago there was an update for the Outlook-HotMail-Connector. Since I was quite happy with this version and it worked flawless so far, I thought that I might give the approach "upload emails via Outlook" another try. This wasn't a good idea, though. I imported some emails (maybe 2 MB or so) into Outlook, moved it into the Windows Live account and pressed "Send/Receive All Folders" - but nothing happened. The emails did not appear on the WindowsLive-email-account, and Outlook kept showing this:
I allowed Outlook to work for a day or so - no progress, no error message, nothing (at least: no crash, with the previous Connector it used to crash for me after a couple of hours). The problem is: I have no idea how to recover from this situation - Outlook will not retrieve new mails in this situation. I tried to delete the newly imported emails and so on - to no avail. The only way in order to recover (that I am aware of) is to delete the account from Outlook, then add it again (and download all emails once more). This takes around 10 hours (not too bad for 10GB), but it works ok (or at least it used to work ok since I had to do this several times already).
OK, lesson learned, I will stick with WindowsMail. It is a pity that I will have to download all emails once more (this time with WindowsMail) until I can upload some new email-archives.