Evolution of my PDAs

In the days before smartphones, the functions of PDAs coalesced into four basic Personal Information Management categories:  Calendar, Contacts, Tasks, and Notes.  Smartphones added email to the list, but Tasks and Notes fell by the wayside.  This is the story of my journey through the available hardware.
Through college and grad school, I kept an insanely complicated schedule on paper.  It worked pretty well.  After graduation, I got my first Palm, and it did the same things but much much better.  I used Tasks to rehab my first house.  Notes was like my personal hard drive, where I stored hundreds of things like my car's maintenance history and which color electrical wire is hot and which is neutral.  I had three Palms, but after some time with a Treo, I decided I didn't want to pay monthly data fees and switched to an iPod Touch.  The transition was not smooth, and the iPod doesn't take well to being used as a PDA.  A lot of the backup and sync solutions were pretty dodgy hacks.  I've chosen the Droid now because I use a lot of Google services.

There are some really delightful things about the Droid.  The app Locale does things like the MacOS 8 Location Manager used to do.  I've often wondered why my Windows laptop is too dumb to change the default printer when I take it home from the office.
(That's the Location Manager module on the Control Strip they put at the bottom of the MacOS 8 screen.  I found this image buried in a help file on a Cisco page.  We have such short memories.)

I thought I was doing myself a favor when I made a point to use Microsoft Outlook to sync all my PIM data between my iPod Touch and my PC.  But it turns out that the Droid's integration with Outlook is no better than the iPod's.  I'm now faced with manually transferring items--for some of the data, one by one--from Outlook to something the Droid has access to.  This feels like a huge miss.

So here I am, depending on technologies whose user interfaces keep changing, that go obsolete, that require me to trust companies with my data, etc.  I actually do trust Google with most of my data, but there are some things I'd rather keep to myself, and for that I want local backup and sync.  I suppose I could go back to paper.  To be honest, it might work just as well.