Always start at the end and work back and try to come back with loops to reduce the length of the hose.
Citing of the vehicle is really important too.
If I can park on the end of a house it can be easier, depending on obstacles, to clean down one side then back up and down the other so I'm only using half as much hose.
Any time the hose gets caught I think about how long it would have taken to get the ladders off and back again, how risky a particular window was, how much damage reaching over the rose bushes would have done me and how long I'd have been climbing on the roof.