2002 Oldsmobile Silhouette Driver's side window (power windows) gets stuck when going up. When I enable the switch to roll up, it gets stuck in a crooked position), so I then use the switch to roll down a bit and then have to guide the window up for it to sit properly. Almost as if it is off track (guides, rollers) of some kind

Remove the inner door panel screws, pry the clips and remove the panel, remove motor, replace with new one, and restore panel

Need to get a wiring diagram. Buy a book and follow the wiring schematic. It should help you out majorly. Can't really work on electrical issues without one.

could be the mechanism is jammed up i would advise you go to a local mechanic and have it looked at .

New switch, and new motor, and still the problem! I wonder if the driver's switch (the master switch) for the pass. window is stuck in a position that won't allow for the passenger switch to operate normally. Not sure how you'd test that hypothesis without trying a new masterswitch, but maybe you can figure a way. And as you know, power for the windows is routed first through the master switch, and then to the other window switches.
I would think you could get the window up if you disconnected the actuator for the power windows. Just reconnect everything after you get the window up.
Good luck, Kollman.

check for a broken wire between the door hindges inside the black rubber boot

Your window switch would be the next thing to check and replace. Both the lock switch AND the up and down switch need to be checked.

I have dealt with this on an Oldsmobile Silhouette...basically the same car. First thing to check is the fuse for the Power Windows, located in the fuse panel inside the cabin (open the passenger side door and it should be on the end of the dashboard). If the fuse is good, there is a strong possibility it is the switch. An ideal situation would be to test to figure out which one is bad, if you have another van of the same family (Olds Silhouette, Chevy Venture). If you can't, the options are to get both switches and replace both, or go to a junkyard and try what you can, or hit a dealership and have them diagnose, but not fix, the problem. Replacing the window switch is cake.

lube the window guides with silicone spray, if that doesn't do it then ou will need to pull the door panel and see what is worn out.

The driver side window switch is the master switch, the power or input to either roll the window up or down goes thru that switch. Double check all the connections on the back of the driver side window switch are good. With a DVOM you can also check to see if 12v are even getting to the master switch in the first place. If you aren't even getting power to the main power window switch you could've blown the power window fuse.

could it be the contacts on the switch are burned ?
place a voltage reader to see if there is power going to it
I bet the switch is gone