I don't know about you, but the quintessential "retro" product in my mind is the record player, and while it might not have "boot times, glitchy screens, unresponsive controls, failed Bluetooth connections, etc.", it's still decidedly less convenient than something modern like your phone + wired speakers. I'm not really sure how reliable wireless speakers are, but in my experience bluetooth headphones are reliable enough that establishing a bluetooth connection is less hassle than putting in records/stylus and swapping them out later. People might like record players for other reasons (eg. they like the ceremony of all that), but I'm skeptical that people like them because they like "having it instantly work".