I guess the issue for me is that I tend to keep contacts and calender notes updated most frequently on an iPod, and in the future an iPad as well. These two devices seem to keep each other happy with iCloud and ios5. I have sort of a dumb but, no doubt, common set-up: an older iMac in the house that won't run Lion and 10.7 so no iCloud there. I mostly use that machine with Photoshop (also on older version). Then in my office I have a 4 year old MacBook that would run 10.7 if I could free up enough space. I do have a few external drives running with the MacBook and intend to migrate to 10.7(if I ever get time).
So the point is four different devices each with its own set of software and files. It would make sense to have some of the data stored on all of them and much of the data archived safely, I guess on external drives, though I had hoped tp make better use of cloud based storage. It would aslo be nice to be able to easily move data from the portable devices directly to the desk machines. I don't find the iTunes syncing particularly helpful. I find it annoying that it only wants to go from computer to device and not the reverse- it seems more suited to helping Apple keep track of purchases then backing up data collected on the portable device.
Sorry to be so cynical. I will take a look at the discussions and 3rd party software you suggest. Thanks again for your help. Nice talking with a real person!
-Richard
ps. Maybe my real problem is understanding syncing. If you add certain data to one machine and certain other data to a different machine before you have a chance to sync, then when you do finally sync, one of the machines will be overwritten by the other, right? I can't seem to get beyond this dilemma...