[Al Skierkiewicz]

Adam,
You have a lot of suggestions. At work we buy the Digikey parts and a variety of different headers. There is also a universal MOLEX crimp tool that was about $59 the last time I looked. Not only does it do a nice job on these connectors, you can use it to crimp PWM pins as well. Be sure that you have the right size for the pin diameter and spacing. They are different. The type you show have a locking option that snaps over a raised flat on the body. This also allows the connector to only be plugged in one way. It also appears that the board may have polarized blocks that assist in the correct insertion of each plug to it's associated header.