The only person that could accurately answer all of your questions, would be someone that is doing exactly what you want to do. If you find that person, chances are they aren't going to tell you how they do it.
1) Any high quality CNC Router can make your molds, but it won't be the fastest. A good mill would be better, but the cost would likely be higher.
2) the best CAD software is the one you like best. You might want to start with Fusion 360, which is free.