I have been implementing a gradual money savings plan to have some extra spending money. When I started about 8 weeks ago, i planned to save 1 dollar a day, then every week increase the dollar amount by $1. On Wednesdays, I deposit the money into a savings account. The planned total amount isn't immense, but it should equal out to a little over $500 to ensure that I can buy some items and eat comfortably for the trip.
 

Done:

• Hotel reservations, badges, tickets, and parking passes all reserved, with badges/tickets and receipts for everything else on-hand and filed away to take with us.
  
• I've booked time off work - with a few days padding on either side. 
  
• I've gotten the dog's booking made at the kennel and took him to the vet to get him up to date on his bordetella vaccine
  
• Got new front tires and an oil change for the van
  
• Everyone in the family has a sufficient new supply of nerdy shirts
  
• Pre-ordered a couple games I really wanted that could be pre-ordered via BGG
  
• Picked up a side project and made enough to cover game purchases at the con - woo!
  

What's uncommon items do you pack that most people wouldn't think of but that you find super useful? I always bring earplugs tp to ensure a peaceful night's sleep in the hotel room (my watch has a vibrating alarm) and a small baggie containing emergency TP because the restrooms at the ICC do run out sometimes. It's saved my butt before (literally).

I don’t stress much about packing besides making sure I have my badge and tickets; just get my things together the day before departure...if I forget something like toiletries/charger/basic clothing items, etc., we’re in the middle of a city! With lots of stores! The only things left are to get the house-sitter booked and get my ish together for the auction. 

Even though my spouse is coming as well, I do agree about cleaning the house before leaving. It really sucks to come home from vacation to a dirty house. 

A small first-aid kit's a good idea. At the very least, band-aids for blisters. I use my multi-tool all the time, but I leave it at home because of the "no weapons" rule.... not sure if the pocket knife-sized blade on it would be an issue or not. I'm guessing not, but figure it's not worth risking. 

Even with a well-broken in pair of boots I always pack a roll of moleskin, just in case. 

I won't pack until the night before, with the exception of my badge and tickets, already tucked safely in my suitcase.

My Gen Con playlist (okay... it's my everyday playlist!):

https://open.spotify.com/playlist/26XSnEhaNbfeOlJPWuG6Lv

Let's see:

Math trade - Talking to a company about sponsoring a raffle. Still posting games and wants. Answering questions about it. Need to make signs and my trade list because the list is finalized on the 23rd.
Playtest hall - Have my games ordered but need to make sure they were printed properly. Schedule finalized. Practicing teaching my game and my "elevator speech" to try to showcase the game to some companies.
Companies - Need to make my list of who I need to talk to at the con. Business cards ready.
Auction - Still packing stuff to sell.
Car - Bought new car (perfect timing; I won't need to clean it out.) Still need to store some phone rechargers in the car just in case.
Tickets - Planned travel time to get tickets Wednesday night (GM badges, can't be shipped).
Maps - All marked and sent to phone for GPS travel.
Cosplay - Need to test our costume at local anime con.

Between today and the con I have this holiday weekend, a library game day, running the game room at our local anime con, a long game day, 7 game nights and 3 D&D sessions. So busy that if it wasn't for the math trade I wouldn't be feeling the effects of GenCon yet.

So I have clients in Indy so I usually make a business trip out of the experience.  As such I'm usually gone for two weeks.  I just pack three bag.  Bag one work stuff suites, work polos, etc... The second bag is workout clothes/nerd attire.  Finally, the third bag is where I store the precious precious games.  I usually send bag one to be dry cleaned while I'm down in Indy so it's nice and ready for the following week when I head out again. 

At any point after the previous year's convention, the first thing I do is play around with my Google Map of Indianapolis, graying out the things I did this year and adding any new things I have heard about (all for the Monday/Tuesday/sometimes Wednesday of Gen-Con week, obviously I am not driving aimlessly around Indianapolis during the convention proper).

In January, when I notice that badge registration is coming up and start putting aside any cash I get in preparation; yes, this means I spend about 2/3 of the year putting aside cash for Gen-Con.  Well hey, I take the 3% discount you get paying in cash at the Auction/Auction Store and a few random exhibitors every year very seriously!

Sometime in late Spring or early Summer I suddenly tune in to granola bar/jerky/other non-perishable snack sales and end up buying enough snacks to last a family of four for a week, so I then usually end up eating about half of my supply by Gen-Con but still have enough left over to accomplish my primary eating goal: save hours every day by living out of my bag and skipping a formal lunch.

I think my last bit of preparation is when I make the challenging call as I do my final packing on which of my ever-slightly-growing pile of nerdy t-shirts to wear to the event.  I know some people wear multiple shirts every day for hygiene, but I tend to bring about 1.5 to wear per day just because there are times you want to wear a Dune reference and times you want to wear a different con shirt; you just never know.

Got my badge in the badge holder along with my event tickets. Got all my nerdy shirts ready to go. A few games for the night before the con. I usually pack my clothes and stuff the night before. Thought my truck was ready to go, but just had the power steering go on me, so having that fixed, tires rotated, and AC charged, because you don't want to drive 7 hours to the Mid-West without any AC... which happens to be my Uncommon thing that I do that others might not think of.

Biggest thing right now is working on costumes for the LARPs I'm playing in.  (french hood almost complet!) and preparing for the LARP I'm running.  Many props to sort.  

I've started picking up the odds and ends for toiletries and whatnot.  And I've decided which nerd shirts to bring, a very important thing.  Planning for snacks.  So many snacks.