You're doing an excellent job, Cliff.

It's important to keep the two ideas, desktop and travel humi, completely separated.
A desktop application is cake. I have no concerns of making that work, and things as simple as counter-sinking the holes would prevent any injury to cigars. It's really pretty easy.
When I start thinking travel humi, a lot of things get tough. Each instance is something that can be overcome, but with every little issue there's more work added, and time is money.
Simple stuff like "what happens when the humi is turned end over end?" I'd have to provide a way to stop the cigars or tubes from sliding. That'd be a pain.
I think I'd taper the holes and send the cigars in foot first in either application, witha foam base for the foot ofthe cigar. But now I have to consider different lengths and rings. That's why tubes and finger bags would help, but that kinda sucks.
It's definately a tough project. I think that's why I'm so drawn to making it work.