Yes, I have Itunes installed and it was entering disk mode just fine. The player was working fine with the original software on it so I figured everything was OK with it (I bought it used).
I took it to work today to try loading Rockbox from there and same problem. So I decided to give up and just convert my files to MP3. Spent the afternoon doing that and loading some onto the player. Plugged the player into my car on the way home and there were no songs on it, anywhere, after I copied about 200. Got the player home and was going to continue loading songs. I plugged the player into my laptop and it popped a message that said something was wrong with the player and I would have to reformat it, so I did.
After reformatting I figured I would try loading Rockbox again and this time it worked no problem. Currently copying my library to the player.
So, for me, apparently even though the player was working fine there must have been some issue with the formatting or existing software that was causing Rockbox install to fail. Reformat solved that problem.
Maybe this will help someone else in the future with the same problem.