Mike,
I have the older "tall rectangular one" also. I experienced the same problem with the smaller drills so I did something very unusual.
I read the instructions.
Plus I called the DD guys about the problem. Same answer.
After you tighten the chuck on the bit, and take it out of the alignment port, look at the end of the bit. If the chuck 'fingers' are twisted, carefully turn the chuck 'nut' (while holding the chuck in your hand) back until the 'fingers' are straight.
This cures the 'backward' relief problem.
The other thing I discovered was that I was not pushing straight in while grinding and I was pushing too hard. It seems that you want to push just enough to make the cam track but not much harder.
I've seen pictures of the new ones and wonder if they've fixed the things that seem to require all the finess to get a good point.
I use the heck out of my DD. Bits seems to stay in much better shape these days......
Had access to a 'real' DD, the Darex, back in the mid '80s and that was quite a machine!
Pete