To be upfront before reading further, I have been using Microsoft based PDA's and PC's for many years. I even build my own PC's.
Having said this, I have at times lost my contacts/addresses and appointments during a sync "last week", which has made me somewhat irritable and down right PO'd. Good news, after a few hours I fixed the problem which was due to Windows 2000, Microsoft ActiveSync and Pocket PC 2003 not being able to play well together. I won't go into detail.
It just seems too much time is spent on making software work and Sync correctly. I think the PDA should work for the Owner not the other way around.
Ok, moving forward. If you are looking for keeping Appt., Contacts and Files, you might want to seriously consider the Palm PDA.
I think that the Palm OS is more straight forward in general use and in storing and retreiving information. I think it Syncs easier as well.
As I said, I personally "currently" use a Pocket PC and find it to be an excellent PDA but, information is sometimes dificult to find or retreive on demand. It seems you have to drill down too much to find something. Excel and Word files for example. Yes, I did and do use shortcuts, but are you sure you sync'd correctly with your PC? Now you have to dig to make sure. Oh, if you file away Excel and Word Files by categories, you better make sure the same structure is setup on your pc and that ActiveSync has the files listed under options to sync said file. No, you can't just drag and drop without opening folders on both the pda and pc. Makes my head hurt. How much time do you really have?
To be fair, I have quite an extensive Calendar and Contact file. I also have quite a few folders by category. I need it for business and need it on demand. Don't we all?
I don't like to negative but the number one problem with the Pocket PC is the availability of the correct version of after market software. There have been so many different versions of Windows CE, Windows HPC, Windows HPC Pro, and Pocket PC making it difficult at times finding one that is compatible with the newest PDA's OS. Can you say upgrade? This is where I think a person can spend too much time looking on the internet for the right software or OS upgrade.
Did I mention you can Sync a Palm with an Apple or PC based computer? Did you know there is more Palm OS based software on the open market?
Go to any online PDA software site and compare the number of available programs for each PDA and OS.
Bottom line, the Hardware is OK for both units. They both are expandible. Check the included memory Size and battery life for each.
It's the software that makes all the difference. What appears to be a good deal can end up costing more.
Did you check out the Tungsten and Zire models?
I wish you well.
Been there and done it too.