There are no dumb questions, 79Trapper65.

1. A brushless motor will allow you to use a lighter, more powerful flight system. You will likely get longer flight times with a brushless system due to increased efficiency as well.
2. ESCs are either brushed (2 wires to motor) or brushless (3 wires to motor). You can't use brushed and brushless together.
2A. The two wire connection from the battery is the main output wiring that goes to the ESC. The smaller 4 wires are connecting to a balancing jack for safely charging the battery.
2B. You should be able to use the LiPo battery once you match the 2 wires to the connector type on whichever ESC you choose.
3. You can use the ESC with the LiPo pack, assuming you pick out a brushed ducted fan/motor setup
4. Yes, you can power the ESC, receiver, servos, and motor all from one battery assuming there is a battery elimination circuit (BEC) on the speed controller and you're only running 3 or 4 servos max.

Feel free to post any follow up questions.