A:Answer if your 5th gen iPad doesn't have a USB Type-A or Type-C port, you will need either a double female USB Type-A connector ("They do exist!" Santa -- M&M Christmas commercial) and a USB Type-A to Lightning cord (ditto/ibid) or a female Type-C to male Lightning connector.
It's been a while since I transferred files between Apple and Windows computers using a non-Apple flash drive, so there might not be compatibility. However, both systems have standardized file systems, so you should have no problems storing your music files on this device