Speaker choices and preferences are totally system and environment dependant and of course personal taste comes into play. But I guess an awful sound will be that for anybody. What works in one situation can definitely sound horrible in a different context.
I'm a bit luckier (or more unfortunate?) than most, having got through an awful lot of equipment, thereby having a fair idea of how a particular speaker (or other item) may sound in my home and on my system, but most people are in the dark I reckon.
It's not unusual for good speakers to not sound impressive on first listen, but have qualities that show when you've got more used to them. Speakers that immediately 'impress', can turn out to be wearing in the long term.
It is impossible for anything digital to sound analogue, because it isn't analogue!