Hi Trek, That is the way I want to do it, too. I plan to get a more general PDA with a bit larger screen. Do you find the QVGA (320x200) sufficiently useful for web surfing? Can you access brokerage and bank accounts? It looks like Vanguard now allows mobile access, I just tried it on my Treo (they had turned it off for awhile).
I really like the idea that you can carry it with you and have it be hidden in your pocket, a huge advantage over a laptop. Also, the cost is less so you don't have to worry about it getting stolen as much. I will probably get one without a keyboard and then carry a bluetooth keyboard in my pack -- they fold up and weigh just a few ounces.
Here are ideas I had for a Wi-Fi capable PDA on the road:
* Web surfing and email, including brokerage account access (brokerage access hopefully rare)
* e-book reading (There is a lot of content now, much of it free, and I just got feedback from Lonely Planet and they are hoping to have some of their travel guidebooks out for testing in an e-book format early next year)
* Public transport database ( http://nanika.net/Metro/
* Language translation (dictionary,flash-cards, there is a "pictionary" like program with useful pictures for rapid visual communication, they also speak and understand but this is more primitive and not there yet, you can even get a scanner to scan in menus that comes with translation software and get an instant translation but again not there yet -- but someday!)
* Playback movies (you preformat these at home and then put them on your web site and/or memory sticks)
* Store my music and audio books for my cheap MP3 clip-on
* GPS (you can get full GPS now with maps, but I am not willing to pay the extra that this costs unless the price comes down)
* Skype, of course!! You can receive calls, too, at your Skype-in number.
* RSS feeds and off-line reading content (can aggregate internet content then read later off-line)
* Showing and previewing my pictures!
Another note -- some of these devices can get bandwidth via bluetooth -- so conceivably, at an internet cafe which does not have Wi-Fi (all too common), you can buy one of those little bluetooth sticks that go in the USB slot of the PC you are using at the internet cafe and surf the web at full speed on your PDA using that PC's bandwidth. This works on the Treo (Palm OS). But I don't know if it works on Windows Mobile 5 (my preferred OS and the most common now for these devices).
The nice thing about content aggregation is that you can just find any wi-fi hotspot out there during the day, download your stuff in a few minutes, and read it later back at your Wi-Fi-less hotel/hostel. You can also read and reply to emails off-line, etc., and then send them when you are connected again.