From what I've read in other posts, I understand that mass uploading isn't recommended in part not to strain the server and whatnot.

Still, it can be tedious and discouraging from doing everything one by one; isn't there a way to at least "mass" upload 3-4 pics/gifs at a time and put them in a queue so that they get uploaded overtime instead of all at once?

You can upload as many things as you want in separate tabs, however, be sure to tag your uploads, or you will be blocked from being able to upload at all.