Or does he just show up when you have something completed for a badge? I want to try and get all of his badges when I restart and if I put all of my bells in at once, I'll get the Millionaire badge before the Skilled Saver badge.
He only shoes up when you complete a badge and if it's not raining/snowing, I believe. If the weather is bad, then he'll appear in town when it clears up. He'll give out the badges in the order that they're completed.
The way he appears is creepy... first he's nowhere in your town, then RIGHT after you do something earning you a badge, you just see him wandering around out of the blue lol :O