A challenge for my techie friends

OK, guys. My head is spinning on this one, and I would value a bit of input from any of my other geek-colleagues.

This is all about my contacts and my emails. Across the years I've come to a few conclusions:

• I like to have my emails on a local machine-based client (e.g. Outlook Express, Thunderbird or whatever). I check my mails using MailWasher before I start and then bring them in; if I'm away from home, I use webmail to look at the inbox and delete rubbish, but leave it on the server until I get home and it can all go in one place.
• I enjoy Microsoft Outlook for two reasons only: its ability to act as a source for a mailmerge (vital for Christmas card labels) and the silly, tiny convenience of being able to pick up an address from the relevant button in Microsoft Word when creating a letter or invoice. I haven't used it for email since I stopped working in an office, five years back.
• I keep a separate Googlemail account for convenience, for an alternative, and for giving out to shops that need it. But when it comes to contact details...
• ...since getting an iPhone, I adore the ease with which my online address book on GoogleMail synchs with the phone - also, therefore, ensuring I have the whole shooting match in at least two places in case one goes belly-up.

One thing I'm always trying to drum into my IT and decluttering clients is the wisdom of keeping single-source data. You can see from the above description that I'm not following my own dictum here. I've been existing on a complex combination of merges and imports for some while now, and it offends my sense of efficiency.

• I want to keep my contacts on GoogleMail for keeping in synch with iPhone, but I don't like the GoogleMail interface for emails (yes, I know I can set up POP3 accounts on it, but I don't want to do that).
• This means that I have to put email addresses into both Thunderbird and GoogleMail when I get them.
• I like using Outlook for the minor tasks described above.

Now, the challenge:

I discovered Soocial the other day. A very neat system (chargeable, but not excessively) it nearly takes care of this problem - but not quite.

• GoogleMail and the iPhone are synching with each other already, so I only need one of those sources to store on Soocial. No problems there.
• Outlook won't synch to Soocial, because it only supports 2003 and 2007, and I'm still using 2002 (Outlook XP) - and I really don't have any other reason to upgrade the damn thing at extortionate cost.
• Thunderbird seemed to synch to it at first, using a rather complicated plug-in called Funambol. I got the initial set of contacts from there into Soocial, no problem. However, since then it's refused to update again - and when I looked at updating Thunderbird from version 2 to 3, discovered that the Funambol plugin isn't available for that version.

So am I looking for the Holy Grail?

• Would it work if I replaced Thunderbird with Windows Live Mail - as that's one of the connections advertised as working on Soocial? Any opinions on that one? I only ditched Outlook Express in favour of Thunderbird, some years back, as I was having an anti-Bill Gates strop at the time.
• Would GoogleMail synch contacts direct with WLM - in which case I wouldn't need to use Soocial as part of the process at all?
• And do I ditch Outlook completely, and accept that I need to export contacts to CSV at Christmastime to make them the source of a mailmerge?

My brain hurts, and I'm sure yours does now. But if any of those friendly geeks out there can come up with a really good solution, I'd be eternally grateful.