A couple of years ago, I wanted my calendars and tasks to sync in both directions between my Mac laptop and my (at that time) Palm Treo phone. I ended up getting it working through some 3rd party software, and it worked pretty well, though it was not a cloud-based solution -- just local sync between my laptop and my phone.

Nowadays, I've got a phone (Palm Pre) that is optimized for keeping data in the cloud -- Google's cloud in particular. Since iCal now supports Google calendar sync, I thought I'd be all set. Sadly, no.

The problems I've encountered:

1. Google Calendar's CalDAV backend (through which iCal communicates with Google Calendar) seems to not support storage of tasks created in iCal. I have no idea what the underlying technical limitation is, but it's listed as a known issue, which tells me it's not a trivial fix.

1a. Google Calendar doesn't seem to support my calendar requirements quite right. What I wanted was my own calendar for my own stuff, and then another calendar I share with my wife for things we both care about (as well as for a "honey do" list.) Of course, the latter is defeated by #1 above, and the former, giving someone else access to a "secondary" calendar in Google and then having that subscribed to and visible in iCal, was a giant hassle to get working, and once I realized I couldn't store tasks in the same shared calendar, I gave up on it and went back to my previous solution (self-hosted CalDAV server.)

1b. I've looked into other cloud-ish task-management solutions like Remember The Milk and BaseCamp, but the former *still* doesn't do 2-way iCal sync (in 2010! I know!) and the latter seems to be waaaay over-engineered for the simple "I want calendars and tasks on all my devices" case, so I'm hesitant to devote a lot of time to it without knowing it'll do what I want.

2. iCal, for whatever reason, doesn't seem to like speaking with CalDAV calendars over my work proxy. I don't know if this is my proxy's fault, but it fails for both a Google Calendar CalDAV account as well as an account on my own CalDAV server that I host privately. I have not found any suitable workaround, which means my "home" calendars can't sync while I'm at work.

3. My work calendar (Exchange) is still going to have to be a one-off local sync type thing. Luckily, Snow Leopard's Exchange support is solid, so it's easy to use a program like Missing Sync for Palm Pre to do this outside the cloud.

I guess I'm just wondering if anyone else out there had run into these issues, or knew of some better way to get this all working together. I know that some of my requirements are a bit esoteric, but we've got some esoteric geeks here, so I figured I'd ask.