Not going to the event this year, but have been to this many times, so I hope that I can answer a few of your questions.
Plan on getting in line for your time slot at least an hour early, but you will make hundreds of new friends to herf with while you wait. Parking can be found easily if you get there by 10am, but it is about 1/4 to 1/2 mile hike to event area. If you plan on drinking, take the shuttle instead because the local law enforcement is just waiting around the event to catch law breakers. Shuttles run regularly and are reliable.
If they are running it like past years, there is plenty of free food and water all day long. Free beer samples too. Plan on spending $20 on raffle tickets to have a chance at the prizes. Plan on buying a cigar sampler or Xikar to get separate tickets for the really big prizes (Jeep, man-cave, etc.). Wear comfortable shoes, you will be standing all day. Take frequent breaks in the food tent. Pace yourself, this is a marathon. Bring a sharpie to get autographs. (Many guys bring their travel humidor to get autographed by all the manufacturers.) Spend time talking to these guys in the late afternoon when the lines are not long . . . they are a wealth of knowledge. However, if you want to talk with Jonathan Drew, plan on waiting in line 2-3 hours. Finally, if you are married, DON'T have your picture taken with any of the dozens of bikini clad cigar girls unless you want to have your wife pull the plug on your plans to attend the next year (did not happen to me, but has happened to a few guys on here)