So far, all I've been talking about is syncing my Outlook calendar with another calendaring service -- Google, Yahoo!, AirSet, etc. What about syncing the other calendaring service with my mobile phone (Windows Mobile 5)? That's a whole different story ... and syncing BOTH sets (Outlook to both another calendaring service AND my mobile phone) is yet another kettle of fish. Finding something that will allow me to do all of that is a bit of a challenge, particularly if I want to be able to sync OTA (Over The Air). See, that's called a 3-way sync: mobile phone to Outlook, Outlook to remote calendaring service and remote calendaring service to mobile phone.
The best way I've found so far to sync OTA is ActiveSync but, as far as I can tell, that only works to an Exchange Server. Mail2Web.com has a free Mail2Web Live account that's based on Exchange You can sync mail, calendar, contacts, tasks, notes -- all of the things that you can sync with ActiveSync BUT it won't sync with another Outlook -- to get that functionality, you have to sync your mobile phone with your Outlook, so it's a 2-way sync -- and that's what makes room for some of these other services. I've seen nothing that will allow me to sync Outlook to a remote Exchange Server, short of actually setting up Outlook to use the remote Exchange Server as its server and setting up your mobile phone to sync OTA (can you sync a mobile device to the same server both OTA and via ActiveSync? -- I don't know!). So, what's out there for use as a remote Exchange Server? MSExchange.org has a decent chart comparing hosted Exchange services, as they're really called, and Solutions Sherweb's service actually only costs $8.95/month -- not a bad price considering what you get (see their web page).
OK, I'm out of time again. I guess this is gonna be at least a 3-part series, instead of 2 -- still have to cover the remote calendaring services that AREN'T Exchange-based.
As part of my overall effort to make myself "location-less", I've been evaluating online calendaring sites. For good or bad, I've chosen Outlook as my "home" calendaring, contact management, task and note system. There's a lot to debate about choosing a "home" system (meaning the system you use to maintain your base set of information and the one whose information is your long-term storage choice) so suffice it to say I'm constantly reevaluating my choice of "home" but, so far, Outlook is the winner. Not for feature set or universality but because it continues to exist!
OK, anyway, on to the real subject of this. I've got a lot of information to post (for me) so I've decided to break this into two entries: part 1 will just cover online calendaring sites and syncing with Outlook while part 2 will cover mobile devices -- syncing and access over the web.
I've looked at both free and commercial calendaring systems. In the free category, I've looked at Calgoo, ScheduleWorld, HipCal (acquired by Plaxo), Google Calendar, Yahoo! Calendar, SyncMyCal and AirSet. Of these, the one that I've chosen is AirSet. Why? It syncs easily with Outlook. It can sync on a schedule or manually and it just works. Plus, the AirSet calendaring concept is a good one -- it was built understanding that we have multiple calendars. This makes it easy for me to maintain a work calendar and a personal calendar. I can have my agenda sent to me each evening, meeting notices sent to me by email or by text message and the layout and user interface is pleasant and easy to use. It understands recurring appointments and the sync from Outlook will carry those recurrences over. The others were in beta (Calgoo) or just didn't carry the ease-of-use that AirSet does (Yahoo, ScheduleWorld), may be orphaned (HipCal) or didn't provide online calendaring at all but just a sync service (SyncMyCal).
I've got lots more to post but have to run off to do some other things so I'll come back to this shortly. Thanks for bearing with me.