Pocket PC Info
Well, I'm not an expert, but the Pocket PC info seems a bit lite, so I'll give it a whirl.
I have a Dell Axim 30. I first purchased PocketMac software. The goods and the bads:
Good: great syncing options - including syncing a specified folder and Mail.
Bad: sporadic recognition that the PocketPC was there - I eventually got it to establish bluetooth connections much of the time, but I never could get it to establish a USB link.
I ended up switching to Missing Sync because of my constant frustration trying to establish links. The goods and the bads:
Good: When I plug the PPC in, Missing Sync starts up automatically, shows me the connection, and offers me the option to mount it as a disk.
Bad: It syncs iCal and Address Book via iSync, but I don't know (yet) of a way to sync files or e-mail. Of course, it could just be that I haven't dug deep enough or gotten the right piece of shareware to do those things. Right now, I'm just thrilled that iCal and AddressBook sync with ease.
As for PIM software on the Pocket PC, I wasn't happy with PocketWindows calendar. I'm very happy with the shareware called Pocket Informant. You'll spend a half an hour playing with preferences, but you'll have a calendar that's a pleasure to use. It's good looking (with your color choices), it follows Apple's philosophy of keeping the interface simple, and it provides tons of wonderful options like having text in the month view.
Now, why the Dell? It had Bluetooth and Wifi. It had Landscape mode. It's well built. It's inexpensive compared to similar configs (I'm assuming the price decrease comes from less pre-installed software - but, frankly, I'd rather choose my own software, anyway.)
The only problem with Dell - you pretty much have to go through them for accessories. All you'll find at the store is Palm, Sony, or HP.
Why PPC over Palm? Pocket Word, Pocket Excel, Pocket Internet Explorer, customizable background, 4 types of data entry with the stylus (including Palm's graffiti, an on-screen keyboard, block letters, and the one I use - which lets you write full lines of text directly on the screen and does a fairly good job of reading your writing. I also have 4 CD's worth of music on a SD media card - making it a poor man's iPod.
HTH
John.