The search for a garage-friendly Outlook replacement

This quest started innocently enough - a desire to ditch Exchange Server and increasing frustration with Outlook. Managing an Exchange Server environment is a big enough job inside an enterprise - even when you can employ someone to do it. Now that I no longer own an international software business, I no longer have someone to run the servers for me - which shouldn't be a problem as theory suggests that life should have become somewhat simpler.

Not so ...

... I have developed multiple personalities - not in the hearing-voices sense but in my professional and personal activities. I'm out of touch with "consultant-speak" but I'd probably be described as a "multi-presenced" individual these days, what with the (now doubled) Maserati role, my music recording and my personal and business roles. Outlook had served me well for many years while I ran my company so, when I became "company-less" it was going to be a big drag to move to a less functional environment.

So, my garage became home to a small Exchange Server environment, initially on NT then a couple of years ago migrated to Windows Server 2003. Running it - especially keeping on top of the patches needed to keep it safe - became what felt like a full time job. It became increasingly obvious that Exchange was not a garage-friendly product. I don't mind if you ask why it took me so long to realise - I'd like to know myself!

What really killed Exchange Server for me was the number of bugs and open exploit holes and the ever increasing cost of upgrading. When it came to a decision about upgrading to Exchange 2003 the cost was prohibitive for my (relatively) humble needs.

The trouble is, if Exchange gets dropped, what happens to Outlook? The answer is that a lot of its functionality disappears. Let me look at what I do and don't like about Outlook:

Things I like about Outlook:

1. It brings most of the info I need daily into one place: Email, Contacts, Calendar, ToDo and Notes
2. Synchronisation between desktop PC, laptop and PocketPC are (suppposed to be) simple
3. It's reliable - even when it doesn't do what it's supposed to it does so consistently!

Things I didn't/don't like about Outlook

1. It really needs an Exchange Server back-end to work as advertised
2. It doesn't handle multiple identities - I need to originate and respond to emails acording to the 'hat' I'm wearing - eg, people who contact me via the Maserati Resource Centre should get messages from my MRC address.
3. I never did get it to integrate all its functions properly - not within itself let alone the rest of the MS Office suite. Even simple tasks (such as dragging an email to a ToDo list or calendar entry) never worked and as for being able to click on a contact to write a letter in Word with the address already copied across ... I gave up writing and editing the macros and VBA to do that after about the fifth change-of-mind within Microsoft.
4. It has no way to easily group tasks and ToDos into projects or sub-headings to cope with the way I work

Without Exchange Server, Outlook loses most of its - increasingly slender -appeal. While email can be stored on just about any server these days using IMAP to leave copies on the server and handle filing and archiving for later use, the same isn't true of contacts, calendar/diary, notes etc. In a non-Exchange environment, Outlook still offers these facilities but stores the data locally on the host workstation PC. Synchronising this data to a laptop and a Pocket PC becomes a royal PITA if you travel as often as I do.

Especially after having been used to it all just sort of happening.