1) What is your dream (it'll never happen, but it is nice to dream) situation for enjoying a cigar? (place, people, drink, whatever it may be that makes it your favorite)
I'm looking forward to my first Cuban Cohiba, smoked on the deck of my new yacht while sailing the beautiful waters of the Caribbean with my wife and a couple of close friends. This will happen when I win the lottery. 
2) What is your dream situation (it happens occasionally, just waiting for the next time) for enjoying a cigar? (place, people, drink, whatever it may be that makes it your favorite)
Hanging out with my wife after successfully installing, training, and leaving a new customer; that's about 2 months of planning and 2 weeks of travel and hard work. My wife by my side, a good cigar, a couple of Maker's on the rocks, Pink Floyd on the stereo - that's a relaxing celebration. 
3) What is your favorite place to enjoy a smoke?
Anywhere with some shade really, but my favorite local place is Sidetrack Tobacco in Bristol, VA. There is always someone there to chat with and their lounge is very nice and comfortable.
4) What is your favorite thing to be doing while enjoying a good cigar?
Focusing on the cigar, with some conversation thrown in.
5) What is your usual pasttime while enjoying a cigar?
Talking, surfing the 'net, reading, watching a ballgame on TV.
6) What is your usual place to enjoy a smoke?
My living room or my smoking room/office/computer room/library.
7) Name 3 people (living) w/whome you'd like to enjoy a cigar?
Uma Thurman, any current or former member of Pink Floyd, any of our troops.
8) Name 5 people from CA w/whom you'd like to herf.
Wow, hard to narrow that list down! Too many people here I'd like to herf with.
9) Name 3 people (no longer living) w/whom you'd like to enjoy a smoke.
JFK, John Adams, François-André Danican Philidor
10) If we could get all of CA together for a herf, what would be your idea of a great herf (site, activities, drinks, cigars, etc... be as descriptive as you can)?
A 50 acre farm in the foothills of the Appalachian mountains here in east TN with tents, campers and bunkhouses for everyone as their preference dictates. Holiday weekend, 4 days of cigars, drinks, food and camraderie. At least one day we'd cook a couple of pigs in a pit, maybe every day! Plenty of room for wandering and walking, hiking the hills and seeing a beautiful place. Or you could just hang out by one of the campfires, shoot the bull and enjoy a stogie. It would be a great weekend.