Recent work and question

Hello everyone, I've been working on headshots part-time for a couple of years now and have even had a few repeat clients. While I do the occasional studio shoot, I have always preferred location work, and working with natural light (augmented by reflectors and a bit of kicker flash). I work alone and like to be mobile, so while I absolutely dig the cinematic look the Dylan creates, managing the gear that is involved (most of which I own already) seems too cumbersome on location. I'd love to learn more about how I can manage that aspect of shooting, as I feel that I can get the expressions and other stuff from my clients quite well now.

So that is my question, how does one utilise lighting gear (eg like Dylan uses in his tutorial) on location, while working without assistants, and staying mobile to use more than one location during a session?

Here are a couple from recent shoots.