Leland is also seen in the Strangerside-mission"I Know You" in the first encounter, where he is about to have a affair with a prostitute outside the Thieves' Landing saloon. The player can give him $10 to encourage him or give him some advice to discourage him.
Hey there, cowboy. It looks like this little ol' article is a bit puny. I reckon you could impress me by adding to it. Don't be shy now. If you're logged in, it'll help you earn them fancy achievements, too.