Using the crack pipe...

I always need a second person. one person holds crack pipe in place with pump and the other actually pumps

most of the ones I've used (usually the little gold ones) are finicky to work with. If you stare at it wrong it won't work. Just take it off and try again until it holds.

It helps to turn it at an angle from the pump head sometimes.

I got frustrated using a crack pipe on my AeroJacket Disc Cover. I enlarged the wheel cover hole just enough so that I could slip my floor pump valve onto the stem. The supplied adhesive covers are more than big enough to cover a enlarged hole. Also my CO2 setup is much easier to use with a slightly larger opening.

Agreed. I was ready to rip the cover off and bag the whole thing. I was in Zone 4 and starting to redline just trying to get that &*%$% thing to stay on and pump up my tire. Finally, I just shoved my pump into the provided hole and got it to work straight from the pump. I didn't even have to enlarge it. It's a little tricky to get off, but definitely better than the crack pipe.

This may be a silly recommendation but make sure the valve is at the top of the tire. I bought my crack pipe with my disc cover, other than occasionally having a hard time getting it to get a seal, haven't had any problems.

First thing I did was to take that nasty tasting black rubber o-ring out of my crack pipe.
Hope this helps.

I have come to the conclusion that it cannot be done effectively by one person. I always need someone to hold it while I pump.

Hold with one hand.

Pump with one hand until pressure really builds, then use your chest or get the craftsman inflatable gun and be done with it.