I would use a new gasket and no lube. The trick is to know exactly where to position the glass when you start, so find a way to lay the glass in the opening without the gasket and square it up, make sure the glass fits the opening then put a mark on the glass and the metal, so you know exactly where to lay it with the gasket on, because once you start pulling then you can't move the glass side to side. Lay the rope all the way around and leave the two ends loosely tied at the bottom center. The rope should just be big enough to pull on without breaking. Set the glass with the gasket on the pinch weld in the opening with the bottom center lined up with the mark and pull the rope evenly side to side with someone applying gentle pressure out side.
If the glass fits the car and you use a new gasket and position the glass right, then there is no reason for it to break.