I put the valve at about 10 o'clock to get the pump head pushed securely on there with my right hand.
I have had some that seem to never quite get the valve engaged, and I've spent 30+minutes just letting air out of my tire. It's the pump, not my IQ.

As for getting tires up to road tire pressure, a taller/larger and rigid barrel to the pump will help make it easier than using a short plastic kid's size pump.