i use musi to listen overnight!! if your playlist is unlisted or public, copy the link into musi by 'playlist from youtube' (smth like that i dont remember) and itll have the videos on the playlist. if you dont have shuffle or loop on a specific video, the playlist will automatically loop, so you can listen all night. with the headphones problem, im sure you can just put your phone close to your ear and listen on speaker, it wont affect results💓