From the looks of your uncrimped hulls they are too long. You should only have about 1/8-3/16" max from the shot card to top of hull, and 1/8" is better.
The better crimper for the drill press or hand drill is one having two indents in the crimper but as stated the hand crimper is faster and does a great job. I have never used any lubricant, the heat generated by the roll crimper is what does the crimping, and being unskived does not seem to be an issue.

David