1: I will sometimes randomly come up with a master for players but usually make them compatible to the player's character's personality. In fact we may make a short back ground story to how they became padwan of that jedi. I will make up the personality of the Jedi Master training the padwan (or when you become a master and want a padwan I'll make up a padwan for you) and what they teach you about the force. You may get a slightly darker master who leans towards the dark side, or you may get a very wise master who completely understands the force, you may get a foolish or stupid master who misteaches you. Just as life seems random yet guided.
2: Yes I will include specialized training.
3: Piloting will be seperate training, regular soldiers are not trained to fly, neither are most jedi. Jedi have trained Republic pilots fly them on missions in Jedi starships. (Remember in ep.1 when Qui-Gon and Obi-Wan were flown in by pilots on a Jedi Starship?) Jedi may learn to fly on their own or even take a corse provided by the Jedi on how to fly, and fly their own Jedi Starfighters. (like Obi-Wan in ep.2)
4: Things like Negotiating and Hacking are not going to be as common as they are in most stories. Simply because in acctual life Negotiating and Hacking are not that common. But you may still learn them in more advanced training like special forces or Republic investigators or from underground syndicates or whatever. If you want to learn to hack or Negotiate, I'll provide you with a scenario that enables that. Whatever you want to do request a sub-plot and it will be done. Like I said, no one has to participate in the main story, everyone can be on sub-plots or side quests and make an appearence in the main plot whenever they want or even never.
The thing is though that I want to do so much but I only have so much time and two hands. If it becomes too much I'll ask for help.