When making your own wire sets, a little dielectric grease around the wire helps it slide through the boot as you're assembling. I use a small set of needle nose to pull it through if it gets stuck in a 90* boot.
Or , u could get MSD wires , they have about the lowest resistance of any made , (50 OHMS per foot) , and have adjustable boots on the spark plugs ends already on them, just have to do the ends for the distributor.
I have mine bent over 45* to 90* and less , thru out the set--------