1. Your habits when planning? ex. Music, drinks, snacks, smoking, etc etc
This one really depends on what level of planning I'm at. Generally, I'll have some classic country in the background, nibble on anything from pizza to fresh blueberries and veggies, pretty casual when I'm going for the general plan. When it comes to the specific plan, I've got my team on teamspeak, we have shared images up on the computer screens, a good red wine and several hours of grinding out the details of what we have, what they have, what can be done about it.
2. How often and how much thought are you putting into it? ex. Hours at a time, a few minutes here and there, etc.
Months. It's pretty time consuming if I'm in a leadership role. I don't want my team to waste time on trivial stuff so I tend to make sure I personally know what the planes can do. Some of us veterans have a reputation of counting bullets. Not kidding at all. Brooke, Flossy, and others, we have spent countless hours literally flying behind a B17 tapping the gun, counting exactly how much ammo takes off a wing, a tail, or whatever. We spend hours launching, forming up, making torpedo runs, whatever the event design suggests is our objective, we drill on it. Not everyone does this, and the event runs fine, it's all about personal choices, I've come up against opponents that put less time in but were quite capable opponents, so there is no one best method.
3. How do you go about planning? ex. Notepads, Pencil and Paper, Type and Revise, etc.
You'd laugh. I have a print shop at my office, so there is the inevitable wall sized map with doodles all over it, multiple computers and monitors on my flight station, wide screen and secondary screen on my primary machine. I'll run PDF documents with graphics, and SIM and I will use the Twiddla map and have the entire team not just talk about what we are going to do, but show everyone on the shared graphic map. It's pretty complex but over the years has become second nature that it's hard to do an event without the massive planning and immersion that comes with it. For me, personally, building the team, training, practice, and all the other stuff make the event for me. The flying part I can do in the main arena, it's planning it out with the team that is the event imho, so I put all I have into it.
Good thing these come around a few times a year, even my wife knows, during scenario season, it's pretty much all I do.