I too, will be a first timer. Me and my husband. Traveling all the way from PA. I have been reading this forum and other posts to help me out. I still feel completely overwhelmed with everything that goes on. I have been to only New York Comic Con, which is huge. But I've never been to a gaming con.  When does event schedules go up and I have heard housing is a b**** to get into. 

Getting housing is easy. Getting downtown housing is difficult.

I am a voice offering a different viewpoint. I LIKE having most of my day filled with events. Yes, I schedule some 'downtime' for wandering, and yes, it can be fun hanging out, but gen con is once a year, and dangit, I want to DO THINGS.

I carefully format an excel spreadsheet, block out times for food and sleep and a dinner with friends, but essentially, everything else has SOMETHING going on, with the exception of saturday morning, where I allow myself time to sleep in. I'm too old now to go 24-7. 

But I've been to a lot of gen cons, and I prefer the ones filled with stuff. I especially wish I had done this my first year, because I didn't HAVE gen con friends yet. I spent too much time just wandering.

What I do not recommend is filling the day without breaks for food and sleep.Therein lies the danger of burnout and missing events. Fill your schedule, just don't forget essentials. And since you WILL make gen con friends, make sure, either with a phone or something, to jot down details. Jim from the cool rpg. Kate from the Mini paint. Etc. With contact info. So NEXT year you WILL have folks! 
 

The last AEG Board game night I got into was in 2015, and I'll list out what was in that box below. There have been grumblings recently that the quality of what you get in the giveaway box declining year after year. I've found this thread on bgg that has a video with what was in the box last year. Hopefully, this is enough to help you make a decision :)

Help me brainstorm other 'big ticket' events guys!

AEG Big Game Night Box 2015 Contents

• A few boards for Trains
  
• Munchkin 'Loot Letter'
  
• Seventh Hero
  
• Junta
  

• Doomtown Reloaded
  
• Sail to India
  
• Smash Up: Monster Smash Expansion
  

Uber is a fantastic way to get the Con from hotels not downtown.  I know many a gamer that have used Uber and they reported no problems at all.

One often overlooked part of con is to find a company or game you like and volunteer for said company or run it! Great to meet other attendees and fill some time while giving back a little to the con. My sweet spot is always part time, i get badge reimbursed (goodies depend on company) and gives me something to focus my con around. One thing i notice about gencon is how many events and the con itself is run off volunteers from the demo monkeys to game GM's to admin staff (red shirts) of gencon itself. If you want something new and to experience con differently i recommend it heavily. 

If you like Pathfinder then I'll echo what some of the previous folks said and recommend Nascrag.  We've been putting on games at GenCon since 1980 - this will be our 38th year.  We go rules-light and roleplaying heavy with an emphasis on fun.

Check us out on Wikipedia or at www.nascrag.org 

My first year I didn't schedule enough.  So I definitely schedule almost every hour now.  Yes, some of those hours should be wander the dealer hall, visit the auction, visit publisher private rooms, meals, etc.  And about 10 hours in the hotel each night for sleep and relaxation.  But overall I really like knowing I'll play X game at Y time so the scheduled events are great.

I always bring a lot of bottled water, and Aleve PM really helps me sleep when my feet and legs are aching from all the walking.

The only must-do event is True Dungeon in my opinion.  It is awesome, definitely try it once or twice (there are 2 different dungeons).  If you are flexible on time and persistent it is not that hard to get tickets.  People drop tickets all the way up to the day of the event.

I have done AEG Game Night multiple years in a row now and the quality of freebies has definitely dropped.  I may not even try for a ticket this year.

Yeah, I actually dropped another event that was scheduled to end at 8 because I was worried about missing the start of Big Game Night.  By the end, I was pretty sure I dropped the wrong event of the two.

As for events, I find that three per day works best for me - one in the morning, one in the afternoon, and one in the evening.  I usually have a healthy mix of board games, True Dungeon, and entertainment events/concerts/etc.  Gives me plenty of time the rest of the day to wander off and do whatever, but having something to look forward to definitely keeps me focused.

I'll try to fit in one 'longer' event during the week, usually a tournament, but that's not 100% required.

"I carefully format an excel spreadsheet, block out times for food and sleep and a dinner with friends, but essentially, everything else has SOMETHING going on, with the exception of saturday morning, where I allow myself time to sleep in. I'm too old now to go 24-7. "

Yes, Excel is your friend!
It helps me NOT overbook, because I have way too many games I want to play / events I want to attend, and if I spreadsheet my days, I see that I may want to have 14 hours of events scheduled straight, but, oh, look, there's no time to eat in there, and I need to eat or I will not enjoy my Con.  Gen Con is also a vacation, so if I am going to have at least one night where we go sit down for dinner, I can block out extra time for that, and to go to church, etc.

Going to be my first time this year along with four other friends of mine - doing most of the legwork for the group and we'll be visiting from Canada. Our plan is to have a friend in the US ship the badges to us to avoid the lineup.

How does the ticket system work? Will the tickets ship with the badges? Do my friends need to have an account with the site to place their own ticket orders, or will it all have to be done through my account?

You _can_ buy tickets for your friends by adding them to your friends and family list, however I'd recommend everyone get their own account as that way you get more entries into the housing lottery, and more chances to get the events you want come event reg.
 

I am so overwhelmed by all of the responses I've gotten here. This is already such different con experience than I've had before; everyone is being so nice, helpful, and it really seems like everyone is dedicated to having a good con experience. 

I'm so excited to be attending!  Just purchased badges, and am starting to get a sense of the type of events we're going to attend. 

Any other advice / input is welcome. I'd like to learn as much as I can before we get there!