I know this is beat to death, but can anyone recommend the best way to convert my iTuens library to a format that will play on my USB stick input?

Can iTunes do the conversion within the program or do I need to buy a different program like https://www.dbpoweramp.com?

I think someone mentioned a gold wing program also.

Oh, and then what do you do when 90% of your iTunes library seems to be on the cloud instead of on your computer????