But surely new technology must sound better?

What new technology? Modern analog gear uses the same classic circuits, but often with lower quality parts and construction.

There is very little ‘new technology’ in analog audio. Most analog electronic circuit designs date back to the earliest days of tubes and transistors. Even things like class-D and class-T amps are not new.

Yes, there are some superb new op-amps transistors and low distortion circuits that utilise them, but you could make a strong argument for the fact that the best analog audio engineering is all discrete component design, with as few op-amps as possible, so this point is moot in the very best gear.

High-end gear often contains tubes and… oh that’s right, all the best tubes are old ones, from the ’50s and ’60s. They certainly aren’t new. Actually, this ‘new technology’ thing is grossly overstated and misunderstood.

Digital is different, but it’s an emergent technology, so you can’t really compare them. Things have certainly improved, so newer DACs often sound better.