Think it's possible to create an add-on that's like a sorta simplified version of photobucket for Vanilla users? Like they can have their own set amount of space and be able to upload files and images in the gallery...
Unfortunately, I can't show the install that I have. But, what I did was install the Attachments feature, and then installed Filebrowser to the upload directory (vanilla/uploads/) You have the manually create thumbnails, but for my use, its really not a problem. I'm not positive if anyone created an auto-thumbnailer-type hack to Filebrowser, but I'm sure it could be done. Then, just give your members access to the Uploads area via Page Manager or something, and then you'd have your needs solved. Maybe create a discussion called image uploads if you don't want a discussion per each upload?