I looked into doing this with one of my DBs and you have a number of options, depending on your budget. :)
The cheapest is to just export pipe-delimited text from the Notepad. The cost of this is $0. The drawbacks is that your users will need to remember the order of the fields, along with what they mean, or risk corrupting your DB. You could also use potentially one of the shareware spreadsheets and export as CSV, which will also elimiate the need for data translation and allow you to create "record templates".
If you want a DB "look and feel", there was a freeware front-end DB creator for the Palm that I played with some. The cost of this is $0. The drawback is that you have limited screen options and its a pain to change (everything is a graphic, even the widgets). I don't remember off-hand what I did to translate the data, since I ultimately didn't go this direction.
Finally, you can buy a more or less full-fledged DB to use on your Palm, which is the way I went since I needed to download records into the Palm and have a local copy of the DB on the PC in case of no Net access (like on a plane or at a client's). The cost will depend on what features you want, but think roughly $20-99 per handheld. The software I used had a desktop client, replicated with the Palm, and allowed the user to save the local DB to a csv file, which is what I used to upload to DBman.
Now, the Palm won't sync directly with your webserver (at least not without some sort of Internet access), so you will need to create an intermediate step taking the data from the local Win desktop to your webserver (which I will assume does have Net access).
There are two basic choices here: 1) you can write a simple VB app to do this (which is what I ended up doing) or 2) you can install Win Perl on each desktop and write a script to do this (which I also did for testing, but the overhead of installing this on all the desktops ultimately ruled out the solution).
If I were doing this application today, I would seriously look at bypassing the desktop and going straight from the the Palm to the webserver.
Hope this helps you start thinking about some of the issues.