Always start in the middle and work out. A heat gun will work wonders, I have one without a heat control, but I turn it on and just flick the gun over the wrap to warm it a touch.
You want a nice bit of stretch to follow the curves and keep creases out, but not so much that the vinyl will want to retract once it cools down. It will take a couple of goes, but it's not too difficult once you get the hang of it