Need general and LB calendar advice/ideas

I'm a long-time LB user who has recently gotten back on the wagon due to purchasing an iTouch to replace my long unused Palm. As a result, I'm experiencing a new era of productivity in my life!

I'm looking for ideas on synching all the various calendars in my and my family's life. This is a little long and detailed and I appreciate your time in reading and considering my questions.

Here's what I'm doing currently:

I set up a Google calendar account for my family then created calendars within that account: one for each family member, a family calendar, birthday/holiday calendar, school calendar, etc. This works well for us as all family members can access and update from their individual computers.

On my Mac I synch iCal with Google using a third party synch tool. I have individual iCal calendars that mirror our Google calendars. That works out pretty well.

I recently tried synching LB for Mac with iCal, specifically synching all of my TLIs with my calendar. The result was not encouraging. LB imported several years worth of calendar items, some were tied to old LB for Palm tasks, some were not. I spent quite a while checking off old tasks, then purging them only to discover that those items then disappeared from iCal (and subsequently from my Google calendar). I have since read a discussion about Mac's synch services v. Palm conduit and understand that this is "normal" behavior. But from my point of view, it isn't desirable.

It also imported all my iCal items into just one of my TLIs. That has me wondering if I need to create individual iCal calendars for each of my TLIs in order to ease synching them. Which has me wondering about the feasibility of synching all those new iCal calendars with my single Google calendar. It seems pretty promising to go from LB -> iCal -> Google, but the other direction...I'm not so sure how that would work.

Then there is finding a good way to synch all that into my Outlook calendar. I don't have WiFi at work. And Outlook appears to want to synch only with the "main" Google calendar, which is my family calendar and not my personal one.

There's just so many moving parts involved in all this, and I am no expert in any of them. I would love to hear your thoughts on how best to organize all of this to most seamlessly and painlessly synch all this stuff up, in both directions.

Thanks!