I haven't seen a video on youtube for this, but here are all the ways to lose that I found:

1. Kick the cat
2. Open the door next to the fireplace in the old house (you will be given some options, but all of them will end the game)
3. Stay in the Old House until 5 o'clock
4. Run away from the mysterious stranger
5. Get 100 demerits
6. Fail the mid-term (Interestingly, this is the only test in the game where failing it ends the game. Failing the first test means you are ineligible for electives but it doesn't end the game. Failing most of the other tests/assignments just makes Gerhard von Urwald unhappy. Doesn't make a huge difference. Failing the final can make you ineligible for Rogue of the Year, or it can get Gerhard von Urwald to say that you need to spend less time on other activities and more time studying, depending on what else you have or have not done throughout the game)
7. Get killed by the Giant Proach
8. Attack the sea serpent while he's conscious
9. Try to walk by the tentacled monster
10. Talk to the zombie pirate captain without having killed his minions
11. Try to open the zombie pirates' chest without having defeated the zombie pirate captain
12. Try to play Poobah with the zombie captain without getting everything he asks for (150 coins and Panda pants)
13. Lose to the zombie captain at Poobah
14. Lose to the Zombie captain in combat
15. Lose to the minotaur in combat (this is a funny one. It's worth seeing)
16. Lose to Zac the Wraith in combat
17. Get crushed by the Golem
18. Lose to the Drat Queen in combat (this is also a funny one. The death message surprised me when I first saw it)
19. Join the Thieves Guild (this is necessary for one of the achievements. It's odd that you have to die to get an achievement.)
20. Don't become Rogue of the Year

That's all I know of. Are there other ones?

Well you don't "die" as such, and based on when this option comes up, I'd consider it more of an alternate ending than a death. It might also be possible to not have this option available, depending on previous actions (maybe?).

That option coming up depends on what you say or do after you get the raven and talk to Shamus. If you give him the raven or if you lose to him in combat, this option comes up. If you dominate him with moxie or if you fight and kill him, this option doesn't come up.

It's been a while since I got this, but don't you see Shawn's gravestone if you do this?

Failing the midterm only ends the game if you also failed the first test.

That's interesting to know. I'm guessing then if you passed the first test, failing the midterm would only make you ineligible for the 2nd elective class.

I have found out that if you failed the midterm, but you passed the first test, you can go to Mr. Urwald's office after the next class and ask to leave the school. He will grant you your wish. The death message is a little wrong though. It says "Shawn was forced to leave the school." No. He ASKED to leave the school, he wasn't forced.

Thanks, I'll make a note to fix that next time we do a content patch. I think two different developers worked on the discussion with von Urwald and the consequences of leaving school early.

I believe you are correct about the midterm - Shawn is not allowed to take a second-half elective if he fails it.

Slightly nit-picky sort-of related note: I'm kind of disappointed that there's no actual "grade" really. I know winning Rogue of the Year makes it seem moot, but it would be nice to know how well we scored in all the various tests. Even if it's only at the end of each test (we're told if we aced it, or if we did poorly, but it would be cool to know percentages/grades/etc - especially since there's no actual "points" score like in the QfG/Sierra games). I know the achievements sort of achieve (heh) this, but not quite - I recall that for most Sierra games, I'd play them through many times to try and get the elusive 500 out of 500 (or whatever the score was).

I agree with this. It's wierd that only the first test gives you a score.

I finally got around to doing this again. you don't really get kicked out of the school, you willingly leave the school and go with your uncle. You and him rule the thieves guild and it becomes the most powerful thieves guild since your father was alive. Urwald gets fired for helping create the Prince of Thieves (you). Terk becomes the headmaster. He discontinues the disbarred bards class. And in the end, an earthquake destroys the town and everyone in it.

So yes, Shawn does die if he joins the Thieves Guild. And yes, you do see his gravestone.

Damn - I must have gotten impatient and just quit the game before I saw most of that. I'll have to try that path again some time just to see this.