It sounds like you're prepared to do some development work. Poke around in the link below and see if there's a program that can be set to drop location points to a data file (output a track file) on a timed basis.
Free GPS Software - An Up-to-Date List
You can probably find one that will drop them into a .GPX file. That's just a specific case of XML ... dead simple to parse for the time/date stamp and location of each data point.
That's all you really need. You can handle the rest ... shipping the raw track file to the server and parsing it for what you want.
Many of the laptop nav programs discussed here can display track files on maps. Some of them can import .GPX files directly.
Garmin's Mapsource has the ability to load .GPX track files directly and display them on maps. It also has a nice set of track editing tools, if that's of use.
If you need to do analysis and presentation stuff and integration with MS Office applications would be useful, Microsoft Mappoint might be of interest. It also imports .GPX files but it ignores the time stamps so you would probably want to pick up a free conversion program to convert to something it would use properly for your purpose.
There are lots of pieces that you can plug together. It just depends on how much work you want to do. Take a look at some of the stuff I've mentioned and see which parts of what you want to do are either missing or not clear to you and we'll see if we can help plug the holes. If you need a consultant I can send you my price list.
If you want a more turnkey solution check out the various possibilities of GPSGate. They have a variety of them.
...ken...