The images don't seem to be re-uploading properly?

This is because the cache will show you the previous picture for some time after uploading. To see the result immediately, you can press ctrl+F5.

I'll add that bit of info to the editor hub as well.

Awesome, thank you! It appears to be working for me now. Didn't realize it was a cached image issue, haha! I'll keep that in mind in case I need to replace another image for any reason.