I’ll admit I work for a RP company but I’ll share what I’ve seen what other people have done and what I plan on doing myself. ( I’m current actually design and play testing my own board game as well. )
I don’t know if you have your heart set on silicone parts, but there are alternatives. Silicone is a tricky medium to cast with. One way to do it is in urethane molds. But also there are very flexible polyurethanes out there that might be easier to work with and get the job done.
Not trying to play the salesman (because I’m not) but you can check out examples here: http://www.interpro-rtc.com/gallery Take a look at the Dog Toy or the Flexible air ducts. Those are both done out of two part urethanes.
I’m thinking of produce my own pieces first in SLA. I’m making them in solid works, and then preparing them to be a mold master. Then within a silicone mold I going to stick 20 of them or so and cast into that mold. My stuff will be simple counters at first.
As to the packaging I don’t really know much about that. I’m playing on selling my stuff online mostly.