For my job I had to upload small handfuls of photos and drawings that were up 1MB-2MB (each) in size. Although I lived in a relatively close-in, modern suburb of a major city, my connection was awful until maybe somewhere around 2006-2007. It was dial-up until the mid-late-1990s and then very poor DSL after.
Eventually I got into the habit of starting uploads before going to bed, and hoping that there were no glitches in the middle of the night.
Also, as I remember, my upload speed was a small fraction of my download speed.