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Like several people I know, I have accounts with Gmail, Yahoo and MSN - and just use them for receiving junk or, more often, to use the chat service that goes with each (i.e. Gtalk, Yahoo Messenger and MSN Messenger). Every so often I open up MSN Messenger (the mac version), and a few times it’s asked me to upgrade (you can’t use it without upgrading). Annoying - but at least they make the upgrade pretty straightforward.
But they’ve seriously managed to make the application pretty heavy - adding a user is a few step process, then the user online statuses seem delayed - and then there’s the sound effects.
And finally, there’s availability. At least it alerts you politely when kickin’ you off:

Software maker’s need to take a lesson from “web 2.0″, and make stuff simple, usable, yet powerful. It’s not hard to do, just think in the right mindset, and don’t forget about your users.
/ok I’m done. And I use skype day-to-day if you’re wondering…
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