Haha! Oh that smoked cheese... At some point, while petting Sir, Riven was totally bombarded with the smell and taste of smoked cheese. And he learned never to bring that point up again, even when the cheese was sitting right there and he really, really wanted some. With her liking him so well, and spoiling him rotten(her and Lin'Lise are the reason Sir's overweight), they'd certainly get on. I imagine their interactions are stiff and formal, from a dog's point of view anyway, when first encountering each other every day until she pays him the sort of relaxing attention of happy pettings and table scraps and then he'd fawn a bit. But as soon as she moved towards something else, like talking to the king, or even just standing and turning away from him, he'd settle down right off the bat. She'd only need to tell him once, maybe twice if she botches it the first time, to stop before he'd learn when grabbing her attention, outside of giving her an alert, is acceptable. 

I can definitely see them running together if she makes that a regular thing, though he wouldn't follow her around too often, unless it coincided with following Erasmus. And dogs aren't bad at being stealthy, inadvertently, but it's not necessarily a big part of their hunting strategy, so if he was getting excited or angry about something and waving his tail around, he might knock things off tables or thunk it against walls or trees. And, of course, nails on stone, while not as bad as on hardwood, can still make more noise than leather boots would. I'm sure he's been trained to be quiet(not being vocal and staying in one spot), but his stealth would be more a side effect of him deciding to go the long way around rather than sneaking past people.

EDIT: And it totally is a great starting post, isn't it? Most excellently wonderful!