Travel Technology - For one-man office: WinMo or RIM?

I am a sole-proprietor management consultant, looking to upgrade my mobile infrastructure.

I've been using the Palm OS for 5 years (Treo 600, 650) with an IMAP email server, and am quite happy with that. (All my email folders on the Treo are always exactly the same as on my laptop). However, there is no way I've found to do over-the-air sync of contacts, appointments or tasks.

So now I'm looking to switch to a WinMo device (Smartphone or regular) or Blackberry. I've trialed BB's before and have liked how solid the operating system is, but have found their PDA functions to be severely limited. Plus, without BES, there's no way to keep the BB email the same as the laptop email. And hosted BES adds about $30/month to the bill.

I haven't tried WinMo, but have heard that it's not as easy to use as the Palm or BB software - many more clicks to do the same things. On the other hand, hosted Exchange (with OTA sync of email, contacts and appointments) adds only about ~$10/month.

Is the BB worth the extra $20/month? Or would WinMo be a better choice? What do other small businesses/sole proprietors do?

One thing to keep in mind:

WindowsMobile devices need a data plan AND hosted exchange ($29 with T-mobile + $10 mail hosting)

A Blackberry only needs the data plan for Blackberry ($20 with T-mobile will get you the Web Client version of the Blackberry push email. But if you want to sync more than just email you will have to look into a hosted BES service, or setup your own).

Yes; the PDA side of WM is much better, but there are some enhancements for the pim on the Blackberry.

In the end it all comes down to the device. A Blackberry is just rock solid and won't need rebooting.

A WindowsMobile device if configured well is also rock solid, but since it is open for third party applications you are reliant on the quality of those apps, and some could crash your device.

If you run a small business, you don't want headaches, so I'd go with a Blackberry. It just works, battery life is better and cost of ownership will be lower in the long run. I'm a big fan of WM, but it does come with a slight learning curve, battery life isn't as good as on a Blackberry and initial purchase prices can be pretty high if you go for a non operator branded unit.