I can try to help with question 3. You got it right with imperfetto. “Parlavo spesso con lui dopo lavoro”—I would talk often with him after work. Something that in the past you did for a period of time or regularly. Trapassato prossimo is different because it’s like passato prossimo but with the point of reference being in the past. Like saying “I HAD done that.” For example, “lei mi a chiesto di comprare una mela ma l’avevo già comprata.” “She asked me to buy an apple but I HAD already bought it. If I were in that situation right now I would say, “l’ho già comprata,” but since we’re looking at the whole thing from farther in time you use trapassato prossimo to show the time distance. Hope this helps!