I think it'd be a good idea to have a way to upload a whole bunch of images at the same time - especially if you're using the same settings for all of the images. I know you can currently drag and drop lots of images into stash, but there doesn't seem to be a way to hit upload for them all all at once, and it takes forever to go through each image individually to upload it to your gallery.
If there's one thing I hate, it's numbers for titles and dots for descriptions. I feel like the artist doesn't give a shit, and suddenly, I don't either.
Having a mass uploading system doesn't mean that this would happen. The titles would probably start as some numbering system like you mentioned, or you could have a screen that simply has a preview down the left of each picture with the forms that we currently use to individualise them, for example "Title", "Description", "Category" (perhaps a tickbox here for "Select this category for all deviations"), and the mature content options. The print and critique options could also be considered, again perhaps allowing the user to copy these settings into all of the deviations.
I think that it's great idea. Sometimes I simply don't want to upload anything 'cause I gotta do it one-by-one. Very annoying. They don't have to remove the current way of uploading, only add the other one you suggested. A lot of my friends who make very nice art simply don't have enough strenght of will to upload every single deviation one by one. And I can't blame them. That option could be like, we upload like 15 deviations, and just edit information later. Someone mentioned titles, that's not a problem. They would be named ''untitled1'' ''untitled2'' etc. and user can edit them later.
I know what you are saying I come across the same problem a lot on my account with me wanting to submit a LOT of pictures at one time. I come across it maybe once every 2 days possibly.
Just an idea