So, in the time since I stopped using it (the last backup file I had was from last march), they've come out with WM6, and there are lots of new custom roms out there for the wizard. After spending way too long looking around for one, and spending way too long futzing around to get them to install (I /know/ this thing used to be CID unlocked, but I still had to go thru the process of unlocking it again to get it to accept a new rom), I found a rom I like, got it installed, and have been getting it customized. It comes with a lot of crap I don't need, and a bunch of stuff I might use later. Grabbed a copy of voice command, which seems to be working quite well.
Now we come to the issue of contact sync. WM won't sync to mac natively. MarkSpace has software to do it. I registered back when they were on 2.5. It caused all sorts of problems, and the most helpful suggestion I ever got boiled down to "clear all your data on the mac, and recreate it". Yeah, fuck you, no.
I pulled down the latest copy, 4.something, and synced. It seems to have worked. We'll see what happens in the long run. But I need to decide when I pay the $25 to upgrade. Do I do it now, so I don't have to actually access the computer to sync (there's a nag screen every time you connect that I need to dismiss), or do I wait until I'm absolutely sure it's going to work. And, if it doesn't work, do I keep using WM, or switch back to the nokia until something better comes along.