With the silicone caulking, the reaction uses water from the air in order to cure. So if you add something that will provide the water to the reaction, then it should be able to cure in a mold, though it may take longer to do so. I have been told that adding Latex paint in small quantities and stirring until a consistant color persists speeds up the process.
I am thinking that I can add the silicone oil and latex paint to the caulking in order to dilute it down enough to be able to pour it into a pre-made mold. If I can get it to cure, with a fairly high level of softness, a high level of stretch, and have no ill effects when it is placed against the skin for an extended period of time, then my project will be complete!
As far as the price of silicone oil goes, it will still be more affordable over commercial platinum silicone and even tin based silicone products that are on the market now.
Thank you all very much for your input, it is helping a lot!