For #2:

Choices (http://macbyrne.livejournal.com/60717.html) by macbyrne: "Written for j2_everafter for Lady and the Tramp. Jensen is not a cocker spaniel, Jared is not a mixed breed and sadly, Jeffrey Dean Morgan is definitely not a rotund Italian who feeds dogs spaghetti." (the hooker part is understated but there, and it's a wonderful, wonderful story)
Shipwrecked by Laughter of the Gods (http://cyndrarae.livejournal.com/71881.html) by cyndrarae: "Jared Padalecki had his plan all carefully laid out - Fuck the guy, keep him facing the cameras, then collect the money and run like hell. It was a simple job really. He wasn't too worried. And they were going to pay him so well... Jensen Ackles prided himself for his excellent judgment of truth and character. It had served him well so far, and he had no reasons to doubt otherwise. So when Jensen meets Jared, he thinks he has him all figured out..."
Once Upon a Times and Happily Ever Afters (http://www.sinful-desire.org/archive/viewstory.php?sid=5015) by j2love: "Jensen thought he had everything he wanted - the job and the girl he loved. But a chance encounter with a hazel-eyed hooker makes him question everything about himself and finally realize things that he's known all along."

Not Gonna (http://archiveofourown.org/works/830531) by fantamae isn't particularly long or angsty, but otherwise fits both requests 1 and 3.