If on #2 you meant do jambs then body during the same paint session, I wouldn't. What I did was start painting and when I got to a jamb or wheel well, I quickly did those first then went right back to the sides without stopping. It worked out good and everything blended in nicely.
I had a helper open close doors as we went along and also manage the hose so it didn't rub or get caught. You could also remove doors and paint on stands but on mine being metallic, I didn't want the paint laying down a certain way on the car and ever so slightly different on the doors. I wanted everything to come out exactly the same for better or worse.