Is your silicone a platinum base? Mine is and I love it because it has such a long pot life and cure time, it can be degassed and any bubbles still left actually have time to raise and pop anyway. Weird part is, it is cheaper than the tin base here which everyone buys because it is quicker setting. I stuff I use is also varible shore, so you customise it from just A15 to A40. When I get around to making molds of my lens parts, I'll be using hard silicone on the outside and soft on the threads inside. Because silicone only sticks to itself, this should just fuse itself together.
The bottle idea is clever. So do you degas before filling the bottle or degas in the bottle? I will have to experiment with that on my 2 part mold. I do think that if I poured less than the amount needed to fill into the open mold, placed the lid in, then degassed that again, I might be able to solve the trapped air issue as it would pull all the air out. I might even have to have a bottle like you have used pushed into one of the fill holes so it sucks rubber into the cavity under vacuum.
Otherwise, I'd have to let that cure and then top up the wings later. Of course that mold is my older V2 (Gen1 soles), so I will need to make a brand new master and mold before making these parts. And of course I won't be doing that until I buy these shoes and given I've just spend a considerable amount on this new Vacuum Form now (to make the tube bags), so won't be buying them anytime soon now anyway.
I don't have a pressure pot as yet and am struggling to find one under four figures that will be large enough to actually hold a decent sized mold. The largest paint pot I have found is still too small. Compressors are cheap. The chambers are not though.