Hey, Joe. Bob's not here today but I'll do my best to assist you.
To start, the major problem seems like the rollers are jumping out of the track. This could be caused by a few different factors and it's not necessarily easy to narrow it down. It's either a problem with the operator or the hinges.
Your first step should be to disconnect the operator from the track and turn it while it's not attached to anything. How does it work? Is it hanging up or skipping at all? Is there any visible damage to the gears or wheel? Or is the operation smooth?
Next, with the operator still disconnected, open and close the window by hand a few times. Does it hang up or drag at all? Does it seem lopsided? Check the top and bottom hinges for any obvious signs of damage, too, or even dirt or debris that could be clogging the works.
There's no exact science for this, unfortunately, it's something you'll just have to garner based on how the window feels. Trying to break down the operation between the two potential culprits is your easiest bet to figure out what's to blame, but if you've never done this before or otherwise have no experience with this kind or project then it may not be immediately obvious to you. That said, there are only so many reasons why a casement window has this problem. 9 times out of 10 it's either the operator or the hinge, so focus your efforts on those components for now.