Well, you know what BOSE stands for:
Bring Other Sound Equipment. Ugh, wouldn't waste explosives on that stuff. Maybe let the dogs pee on it. Heck, if I'm feeling in the mood, I would do. Just hate the high levels of distortion, cheap parts and high over-pricing. I've also never seen any system be out of phase with itself before. But that's just technical engineer speak.
For the most part, you're going silent on the stage. And with those BOSE units behind you, you're getting that as your monitor as well. Thought about mybe getting in-ear monitors?
Multiple choices. The Punch pros are light. You can get a tripod stand that goes up to 12-feet, be super light, and then put an o-clamp onto the Punch Pro. I'll test this with my Crank2 stands later and report back tomorrow to see if this works. Otherwise, get a full T-Stand. Throw the cross-bar onto the stand, put the light on the T-bar, tighten screws, and raise it up. Bring a few power cables, and a dedicated and MARKED DMX cable that can go up and down the full length of BOTH stands and hve slack and span the gap on the ground(or behind you) and you're good to go. Say, a 50-foot cable should suffice quite nicely. You could also use the bolts to attach it to the T-bar, which is all well and good, I just like to have stuff like that come clear off the rigging between events. I'd say 2 of you could set up the lights in 5 minutes, one on each stand. Depending on the size of the stands, you can get cases for them as well.
I'm guessing that with a little practice, you'll spend way more time looking for power outlets than setting up your lights. At the description of your rigging, 1 15amp circuit is more than sufficient for your entire gig. Figure out your "wiring methodology" and buy power cords that match. Get some reels to wind your cables up onto fast and it should go smooth.
I carry my stuff around in a truck. Quality first. The rest is secondary. Considering my console weighs 400 pounds in the case with cabling, I ain't putting that IN my car, much less a passenger seat. It's wider than my car, but has a couple inches to spare in the truck(side to side).