If you have an old iPod and there are music files that haven't been transferred from computer to computer throughout the years, it is time to back up that library as soon as you can. If you use a Mac, there's an app called Senuti (iTunes backward!) that can help with the process. For Windows users, try YamiPod. At the very least, back up the iPod onto your computer with iTunes via the "Back Up Now" function. Don't lose those years of music tracks!
If you upgraded to macOS Catalina and wanted to continue using an old copy of Adobe Photoshop CS5 normally, you're probably out of luck. 32-bit software, like Adobe CS5 products, is not compatible with the newest Apple Mac operating system. Unfortunately, nowadays Adobe wants customers to subscribe to their Creative Cloud (CC) service to continue using their latest and greatest products. Alternatives to common Adobe-related tasks include Affinity Photo and Smile's PDFpenPro.
Charles has upgraded to macOS Catalina 15.1, and now he's getting crashing due to an error with an iOS device. Leo suspects it may be a wifi sync issue between Charles' iPad and the Mac. So into the music settings and turn off sync library and see if that solves the issue. It sounds like a bug that Apple has to fix. Also, try opening the Activity Monitor. It'll show what processes are running and when you shut down, kill the sync process. That's not a great solution long term, but it could work until the fix comes in a future update. A complete clean install may also fix it.