I did a fair amount of testing and never ran into the issue, so nothing comes to mind as to what could be causing it. For one reason or another though, the script must determine that you already have the correct equipment on you or you have chosen not to upgrade items. On start, the first thing it should always do is check your items and equipment. It's probably something silly that I missed.
If you have any suggestions for new training areas, I'd be happy to add them. When/if my Git application goes through, I might make another version of it which would include members, which would be premium.