Coming from a BES ecosystem where everything just worked automagically, it’s a bit of a shock how kludgy everything is now that my primary computer is my laptop and I’m not auto-syncing over the air for every calendar or email update.

Plainly put: in comparison to the magic auto-sync I had before, this USB connected pocketmac/entourage solution blows.

I’ve spent the past couple days experimenting with different variations of Google Calendar, Mail, Entourage 2008, iCal, Thunderbird/Lightning/Provider, etc. but so far I haven’t hit upon that ease of over the air automatic syncing that prevents me from doublebooking a time because I entered one event into my blackberry this morning and another into my laptop this afternoon.

Frustrating.

If anyone has any recommendations I’d love to hear them, I think the closest I’ve seen is actually Apple’s MobileMe, and if that’s the only real solution then I’ll get it, but it would seem to me that there’s got to be an easier solution to the problem of a two-way updating autosyc between two very common hardwares, and several variations (or even just one variation) of very common softwares.

[edit] Today I’ve been trying out Thunderbird and Lightning to sync to Google’s Calendar, and then using Google blackberry Sync to keep the handheld in check, however that only seems to update the handheld, not push information back to my laptop or Google so that everyone knows what everyone else is up to.

This is making Palm’s cloud solution even more appealing.