Not exactly #2 but close enough:
Knowing and Seeing by emebalia.
Summary: Bobby knows and it's about time to let them know. In his own way.

https://www.fanfiction.net/s/9154378/1/Knowing-and-Seeing

aw thank you. That one was cute

In response to (3): choosing my confessions (http://de-nugis.livejournal.com/58842.html). It's unrequited wincest, but it features Cas domming for Sam in order to help him deal with his feelings about Dean, so it seems like it might be up your alley.

Thank you! I hadn't read this one yet!

#5 In The Blink Of An Eye (http://archiveofourown.org/works/1033262/chapters/2059201) Chad is in love with Jared, Jared is in love with Jensen.

#6 I have a fic rec for CWRPF at Astrozoot's Completely Subjective CWRPF Fic Recs (http://astrozoot.livejournal.com/3437.html) which has a bunch of Chris/Chad and Jensen/Chad.
My favourites are Loveland High (http://archiveofourown.org/works/289320) There's a new boy at school, his appearance sets off just the faintest ripple through the students of Loveland High School. (Evenly splits it's time between Chris/Chad, Jensen/Jared and Mike/Tom)
and one of my absolute favourites (Christian/Chad) The House Rules (http://archiveofourown.org/series/13674) A novel length story of a struggling country singer and the young man who tries to change his life.

Awesome thank you!

1) The Things You Know Can Kill You Stone-Dead (https://www.fanfiction.net/s/9902271/1/The-Things-You-Know-Can-Kill-You-Stone-Dead)
You and Me (http://exd-fic.livejournal.com/51543.html#cutid1)
To Make His Children Happy (http://hellesofbelles.livejournal.com/30819.html)

3) Sam/Castiel (http://previous.delicious.com/chellexxx1/Sam/Castiel+D/s)

4) Sam/Gabriel (http://previous.delicious.com/chellexxx1/Sam/Gabriel+top%2521Sam)

5) When Things Come Crashing Down (http://angels3.livejournal.com/12811.html#cutid1) by the brilliant angels3 an epic story where Chad is great

The Shirtless Welling Drinking Game (http://www.sinful-desire.org/archive/viewstory.php?sid=3093) by the talented pair cha & anyothergirl415

anyothergirl415 writes Chad/Chris Kane too here masterlist415

I have a Chad tag, where he appears in the fic in some respect here (http://previous.delicious.com/chellexxx1/Jared/Jensen+Chad%2521Michael%2521Murray)

xxx

For #2: Not Broken (https://www.fanfiction.net/s/7494672/1/Notbroken) by paperstorm
Summary: Bobby catches the boys in a compromising position, threatening the end of Sam and Dean's relationship with him.

I have one that's a mpreg where Chad is pretty awesome as a friend. :) I know not everyone is into mpreg but here's the link in case you want to check it out.

http://angels3.livejournal.com/40403.html