Using Microsoft Outlook with the Internet in mind

I’m currently using Outlook 2002 which I can synch with MyYahoo to get web access to e-mail, tasks, contacts and calendar, as well as some sharing abilities. BTW I can’t believe the best things at Yahoo are free, but that’s not the topic at hand.
What I’m looking for is more integration between Outlook and Windows Messenger, specifically at the contact list level.

So far, I’ve only seen Messenger in Outlook at the contact (detail) level, but that’s hardly enough (and it requires you to add your correspondent e-mail in a separate "Internet Email Address" field). The other place where Messenger appears is in message headers, but apparently only if the message was sent using the Passport e-mail.
On one hand I don’t want to mess with an Exchange server for my simple home office/virtual team needs, on the other hand most MSN addons are not exactly made with professionals in mind. Any suggestions? Browsing and searching the Outlook newsgroups (such as .contacts and .interop) didn’t get me anything so far, nor did the web at large.
Now that Messenger handles IP phone calls (I just signed with Callserve) as well as whiteboard, application sharing, audio and video conferencing, it really makes sense to use it from Outlook (and obviously then, from the Contacts list). Some of these things you could do with Netmeeting (and a right click on an Outlook contact will indeed propose it), but this program has always proved reluctant to be tamed (ie. configured and used), at least it was always a pain for me.
One of the big strengths of Outlook is the integration between its components. For instance, it’s very convenient to drag an e-mail to the task or calendar shortcut to create a pre-filled object in these categories. Instant messaging should be considered as another category inside Outlook, in order to let it flow within the overall working environment. And I’d rather not wait till Microsoft acquires Groove.
One application would be to journalize and log chat sessions in the same way you can already track e-mails and phone calls for each contact. Since Microsoft has been researching voice applications and collaboration for years, please throw in voice-call logging (to mp3 files) and voice-to-text transcripts as well, so that we can asynchronously share conference calls with people that couldn’t join (and refresh a failing memory).
Instant messaging and IP telephony have to be enabled within group collaboration and workflow to give users the productivity boosts they promise. Though I don’t want to talk to my computer (it’s slower than using a keyboard, and I don’t want to talk all day anyway), I do want to digitize selected speech to turn it into a electronic "paper" trail. The complimentary nature of VoIP and IM didn’t escape France Telecom which invested in Jabber a few months ago. But VoIP should go beyond cost-cutting and allow better online collaboration as well.
So close, yet so far. It’s not that Microsoft doesn’t understand the need to extend Office with online services, but there’s not much to use yet. Below is a (lame attempt at a) fake screenshot to illustrate part of my point.