I don't think the resolution will effect the upload (unless it's stupidly high, affecting the files size), but the file size will. The max file size is 2 meg, but that should be more than enough for run of the mill photos.
The system occasionally times out when I try and upload but that may be more to do with file size vs upload speed.
I notice you've been uploading one of the files I posted in this thread. I did say they had already been uploaded to the wiki, but it's not an issue, they will just overwrite.
If you want to check what photos are already on the wiki, once you are logged in go to "Special pages", "Gallery of new files" and they are all listed there with thumbnails.
Have another crack with a new photo ... it would be helpful if you could upload the references for the schematic you require.