Quoted from Mitch:You really need to buy a ratcheting crimper thath doea the wire and jacket at the same time. They arnt that expensive and will save tons of time, plus they hold the new contact so you only need one hand on the crimper.
This is the ratcheting crimper that I purchased a while back and it works great. There are several YouTube instructional videos for using this crimper. From someone who couldn't make a proper crimp to now making perfect crimps I can tell you that it is well worth the cost.
https://www.amazon.com/gp/product/B00OMM4YUY/ref=ppx_yo_dt_b_search_asin_title
Gord