I always thought hotmail is one of the worst free email services, but I decided to give it a try when I joined Microsoft and was able to register a nice address with the domain live.com that had just been released. Now I am trying to get rid of it using a custom domain along with GMail. I am very happy with the decision so far. And for the first time I am even started using Google Talk, providing a more efficient communication and clean user interface than MSN Messenger. Even the Outlook Connector ended up being a way to move all my email from my live.com account - probably something Microsoft didn't thought about, otherwise they would have blocked in some way.
What just made me mad - and it's not exactly surprising giving Microsoft's records - is that you cannot forward your hotmail/live.com emails. Usually the expected is that they don't have this feature, but they DO. And email is only forwarded if you are forwarding to hotmail accounts. This is just stupid - and another attempt to lock you in. First, you DON'T have POP, you DON'T have IMAP, and by using a proprietary protocol, you only have two options to access your email from a client program: using Outlook with a plug-in (Connector, which doesn't have exactly the best performance) or Windows Live Mail. No other option. I accepted these limitatinos since I am working at the Office group and have been trying to use Outlook. Not being able to forward your emails though just proves the point of everyone that criticizes Microsoft. Had they been offering a good service - and would first implement the very basic feature of checking for the new emails automatically without requiring the user to click "Check Email" all the time - more users would be using their services and no lock-in strategy would be necessary.
Other complaint from my 11-month experience with Live + Outlook is the way junk email is handled. If you have a false positive, when clicking on the "Not Junk" button, you always get a dialog saying "so now you trust all email from this address?". If you click "no", it doesn't move the message back to the Inbox. You MUST add the sender's address to a white list. I don't want to have a white list to do that, but that it learns to recognize the email contents to do a better work at recognizing actual spam.