Not to fan the flames, but I think it's much easier to be a travelling minstrel if you're broke. I've met a lot more homeless people travelling from city to city and making a living playing music than I've met people doing that who were well-off. If you're moderately rich then you're likely to have a job and they won't be happy if you just skip town. If you're really rich you're still likely to have obligations that are going to prevent you from doing that sort of thing.