This is my first time using silicone to make molds, and so far, the results are great. I didn't use any release agent and the casting came apart easily. Also, I did not vacuum degas the silicone. After the liquid silicone sits for a while, all the air bubbles will rise to the top. I also tried applying heat to make it cure faster but the results were terrible with lots of bubbles. So just letting it sit at room temperature seems to work well. One thing to note, however, is that most SLA resins appear to be incompatible with platinum-cured silicone, inhibiting its proper curing.
If you cannot drain all the air bubbles, you can punch holes at high points in the top half of the mold to allow the air to escape. You can make them large enough to put a funnel or straw in the hole to hold the excess silicone while you fill it with the caulk tube (assuming that's how you fill it). For surfaces where the 3D-printed resin model is not compatible with platinum-cured silicone, spray it with clear wood lacquer. We use this method every day to make silicone molds from SLA castings.