Are you trying to upload the track layout or the track pic that shows up on the "Home" tab for the next race?
Either way, I think the problem can be the image proportion (one is 520x310, and the other 500x310) as they are quite wide and the profile picture shown is squared in the standings.
Test a different picture with a more squared or vertical proportion (mine is 430x640 and it worked, so you can even try with this Mexico picture, just rotated 90°) and the same file types (.png and .jpg) to see if it will upload. If not, then it might be a bug ?