Considering python - have a few questions.

[Simon John]

I'd go with a MySQL / Python / Apache route, but if it's Windows, maybe
not.

Also, you shouldn't store images in a database - images should be on
the filesystem with their paths stored in the database.

I'd definitely say going the web application route would be easier (and
more portable) than the GUI route, and a free Windows PyQt is still a
long way off, so stick with wxPython if you want a non-web GUI.