Thanks for the help, I have deleted the app and also re-downloaded the .gpx files to my computer. I'll try the sync route first and if that doesn't work I will try to download the files directly to my iPad.
I am of the mindset that if I do something as simple as change a route color on my computer it should also change the route color on my iPad when I sync it and it does not do that.
Generally that's how it should work, and how it normally works. However, sometimes it seems to get bogged down with it's inability to support syncing (maybe Outside defunded their servers? Or it got more popular?), and sometimes it'll say SYNC COMPLETE when it's actually not which is super annoying.