No the machine doesn't need to be level but the closer the better so that your not fighting to many variables at one time. Usually there us a close enough to level area near your bend. Just put your pipe in do a pull get a degree or a degree and half whatever the inspector wants then before you release the pressure from the shoe check with your digital level on the winch side and subtract from the back side which if you need to get a high number of degrees will end up being in air pretty high so get your ladder and your help to hold it for you.
On a different note if you have to engineer the bends, over bends, sags and rolling offsets than you could be in for quite a ride. But if someone has already engineered it then practice on a pup piece to get familiar with your machine then have the inspector there measuring the deformation and telling you how many degrees per pull.
And really watch your seams as they need to be on to be on top.
Operating the machine isn't that hard but I've never worked with a mandrel Ice bent 8",6" and 3" with a machine and a shoe. I also agree with Pipe head about the engineering part that can get tricky but it's not too complicated if you can work with an old timer to show you the tricks.
Also don't forget it's not just bending but you also got to account for overlapps in the pipeline and you have to be on the stringing crew to string the pipe proper. So there is alot to consider
Also