I have a budget in Excel, but otherwise I can't say that I have anything else in a spreadsheet.
I have a List called Vacation, and I never delete anything from it. Every trip a few days before I go through and uncheck the items I need to pack for this particular trip. Then I can re-check those off as I go. Some trips don't use everything (I probably won't bother bringing an e-reader and use my phone if I actually get that desperate for something to do), but at least it's there, and I can just check leave it checked if it's not required. Next trip, I'l be able to decide on it without needing to constantly tweak my list of possible packed items.
After the SouthWest debacle where you couldn't get through security unless you already had a bar code handy, I always print my tickets if I'm at home, and I'll print the hotel confirmation as well. I also pack all my clothing into packing cubes. If I find out 3 hours before my flight (or even at the air port) that I have to ditch from checked luggage to carry on only, I can move all the clothing, etc, easily, and toss out any larger sized liquids I may have been indulging in. (Everyone brings a mostly empty suitcase to Gencon, right? Right??)
My calendar is in my phone, with all the event locations. This year since it's just hubs and I and we're not doing anything separately and it's a light schedule, it was trivial to add stuff to a trip calendar we both share. Previous years my detail oriented coder friend took care of the group's calendar getting into Google. Flight check-in reminders are there, along with that stupid code you need for the app to actually do the check in process.
I have the official fancy pouch lanyard from a few years ago and we use that for tickets and badges, with the addition of a Pin piercing the top of the badge holder and going through the badge opening so as to ensure the badges stay put when you flip it upside down to open it (brilliant design choices there). Otherwise the zipper pouch is perfectly adequate for securing tickets.