1). I'm not sure if this was Wincest or not. I vaguely remember there being a Wincest and a Non-Wincest version, but they could just be similar stories. Dean is at Stanford with Sam. He's going to Sam's classes with him and they talk a lot about it. John visits eventually claiming that there is a case at Stanford. He notices how close the boys are, but I don't think he minded. It turns out that the professor of the class the boys go to is a ghost. Also, I kinda remember Sam giving Dean an engineering textbook that he takes with him when he hunts. Sam finds it later with notes inside and missing pages. 

2). Jensen's family goes to their summer home every year, where Jensen is good friends with Jared. It shows their friendship for a couple years, until Jensen realizes he's in love with Jared. He gets a wedding invitation that he believes is Jared's, but is actually his sister's. Jensen avoids the cabin for a few years, until his brother kidnaps him and takes him out in the back of his truck. I remember something about Jared living in a tee-pee out in the woods. ***FOUND!! Link in comments!***

Any help would be appreciated! Thanks!!