My goal was to be able to use the last version of iTunes that can purchase, update etc. apps from the App Store. iTunes 12.6.5.3 for Mac is no longer able to download from the App Store.
I was able to get iTunes 12.6.5.3 to run quite nicely in Crossover 22 using the following recipe:
Create a new 32-bit Windows 7 bottle.
Use Crossover's install function to search for and install Platform SDK Redistributable: GDI+
Install the 32-bit version of iTunes for Windows 12.6.5.3. Install as an "Unknown Application" - not using the Crossover search method. It's available directly from Apple HERE
If your iTunes Library isn't in your Home/Music folder, create an alias there to where it actually is. I don't know of a way to get the Crossover iTunes to look elsewhere. Yes, you can change paths for Music in Wine Configuration.