Re Lasers: I've seen Lightburn come up a few times and given that canning and labeling are more core to the business (and the constraints on our space), I will probably go ahead here. Boss and Cloudray look like much better vendors than what I've seen so far. Most of the desktop laser brands I've founds seem like thin website wrappers over an Alibaba/Amazon backend, and I don't mind paying extra for support.
Re CNC: I also think the general advice here is probably right. My needs are pretty simple so the price and seemingly high flexibility of Shapeoko-level stuff tempts me to DIY, but it's also probably easier to outsource. I am just not sure where to look for a real-world machine shop that can mill these for me. If you can think of a reliable forum, online community, or vendor that doesn't force me to learn just as much about designing pieces as DIYing, I'd love to know.
Thanks all.