Ok, I think I read in another comment of yours that your talking about 550 tracks in collection? At such a low number I'd skip the playlist management and just

Ok, I think I read in another comment of yours that your talking about 550 tracks in collection? At such a low number I'd skip the playlist management and just sync the whole collection. At that point it's a non-issue as everything gets synced witout the need for any action on your side. I only buy lossless music from third party stores and physical sources and therefor only use iTunes for music management (without problems I might add), not for buying. However if you often buy from your iPhone I'd guess it's even easier - shouldn't your album/song already be on the phone immediatelly after purchase while any other changes get synced whenever you're in the same network as your laptop? I still fail to see the issue here.