I find the chucks with the inner wheel end straight on rather than angled are more convenient than those with both angled. I suppose that may well vary with the specific wheel design you have. Either one can work, but might require more or less fiddling around to get a good seal, possibly including reaching around between the tires with the other hand to guide the chuck and valve stem into alignment.
Air-through valve covers are a big help; besides not having to unscrew the valve cover (and you really ought to use some sort of a valve cover), they effectively extend the stem a little bit and that little bit helps. I have Alligator brand ones and they seem very well made.