Yes, and yes. The only difference between them is that the desktop version contains the xsp web server binaries while the version for maemo you install xsp deb.

Actually the XSP web server is a mono/.net program itself so when you run this on desktop your running the exact same webserver .exe as maemo except on windows desktop xsp bytecode would be run by the official microsoft .net framework.

Running off your tablet you could go to a desktop and hit the device (if you know its ip), load the larger editor (scaled for desktop) and compose html documents referencing images on the tablet, and save them to tablet itself or download htm. Then you navigate to the documents screen and click on the document and you've basically made your own web page. You can also upload images/music/files to the tablet.

All that works the same on the desktop except in reverse so your IT can easily get access to whole directories of images, files, music, etc.

Running off your desktop it would work the same way, in reverse. This first version only currently supports single directories (not subdirectories) so dont go too crazy and copy your whole mp3 collection to music directory (unless it all fits in one directory). Perhaps future version will support subdirectories.