[Ninjavenom]

It depends entirely upon who the person is. For example, some Nords are meh to boasting, some love it, some hate it. You've just gotta try them all.

Also, to anyone who's lacking fundage, try joining the Morag Tong. All you need to do is kill an innocent person, and their guildmaster approaches you when you sleep. Once you join, you can run about ten missions, each with a bonus prize for killing the mark/s a certain way, but you can still collect your money by straight up murdering the hell out of them. All of the bonus prizes are geared towards assassin characters anyway, so some of you may want to skip them. Anyway, once you run the last mission for your first Brotherhood Sanctuary, the next mission gives you both a large, empty place to live (well, you have to make it empty) and a horse named Shadowmere. So if you're not trying to drop a lot of dough on a horse or on a house at first, just run these missions first. Anything requiring stealth can just be chameleon or invisibled through, for our barbarian friends.


edit: cool note: After the second mission, try not to talk to too many people about your mark. Sometimes they do an awesome job of making you feel bad about killing them.