Lol all your ways wont work the way to stay up past 2:00am is to go to the mission Final Showdown when running up jump from the nearest edge make sure it's low and not a tall edge when doing so you will end up on the bottom of the bell tower and the schools roof walk around for a few minutes and notice that the clock usually disappears. Jimmy during this mission and the mission Help Gary and the mission where you do an errand for the teacher are all ways to stay up before the time. Also the best way to stay up before 2:00am is to start the mission Halloween Jimmy instantly past the clock and their is no way to sleep he can stay up for long periods of time a weird glitch but it's fun during this mission the Dropouts have a city spawn point lol.