Slow and Buggy Image Uploads

This has been an on going issue. Uploading any images either directly to the map layer or through the Upload option takes easily 5+ minutes if it doesn't just freeze (sometimes on a refresh it's there and other times its not). I've tried disabling all plug ins. I've tried three seperate browsers. It's really making it so I'm looking elsewhere for a VTT. These files are tiny and already in jpg format. (1MB or less)

Hmm. I don't know how to troubleshoot what's going on with yours, I can only report that my Uploads have been fine, normal, and tends to finish fairly fast (around 5 seconds, up to 30 seconds for a larger graphic). Much-longer for an animated map on Classic non-Jumpgate (because roll20 does some strange background conversion on it).  Are you on Jumpgate or classic? 

Im currently using Jumpgate. I got in the habit of making sure any image uploads especially maps use jpg since from my understanding it's roll20's preferred format. I use GIMP to transform and export the image in that format if it makes a difference.

I'm not too sure how to resolve this myself. If you suspect your images, you could try uploading a random small JPG from google that's not from your GIMP but i seriously doubt the issue is your images (since you said they are small file size and JPG). It could be something else, like Jumpgate issues, or your internet connection, or some sort of converter or cloudflare on Roll20's end, or on your browser. Best i can do is assure you this problem is not across the board for me, so there should be a solution out there. 

Another test is to use a private browsing window to rule out most extension conflicts. Flush cache and cookies is also a good thing to try.