1) when monologuing
2) when realizing something, with confidence
3) when expecting a reaction from the other party, or simply leaving an aftertaste
4) 더/던 is for the past tense. as for the rest, they are too many
5) 랴 is equivalent to 느라, and it means "due to"
5) 리라 is monologuing in a pledgeing form
6) asking for an approval/opinion
7) correct
8) ???
9) correct
10) used to. 내가 몰던 차 = The car I used to drive.
11) similar to "는 것이". 집에 가기 두렵다 = I'm afraid of going home.
12) resulting in 밤새 일하다가 지쳤다 = I'm exhausted as a result of working overnight.
12) an action that gets interrupted/calceled: 집에 가다가 돌아왔다 = I returned from the way home.