6000 songs? Blimey, I’d have thought that those would be more than adequate on shuffle; I’ve got around 2000 on my old iPhone that doubles as a satnav/iPod, and that’s fine, I’m not listening every minute of every day. Still, a lappy isn’t going to add a huge amount to your baggage, so it’s probably the easiest way to a quiet life, everything else is complex, phaffy, and adds expense, like data costs, or external drives.
If he was using a Touch, the option would be a wifi-enabled external portable drive, a 1Tb version’s available, and he could stream to the Touch, his own personal local ‘cloud’, but that won’t work with a Classic.
It’s what I’m thinking about doing to overcome the space issue now my Classic’s damn near full.