Hi.

My spouse has been wanting to come to GenCon since before we were married. Next year is our 20th ann and I want to surprise him.

I am clueless and I don't know what to plan for or expect. I have never been to Indianapolis.

I have our transportation and our hotel booked.

I know I need to buy badges when they are available.

What else should I be planning for and budgeting for?

How much is parking per day? 

And can you recommend a nice restaurant for our anniversary night?

Thank you for all help you can give.
 

We are talking about 2018 Gen Con here, yes?

I'm hoping that someone else can take the parking question; I have no clue.

Forr the restaurant, if you're wanting to go fancy, St. Elmo's is an upmarket option. Servers in suits, that sort of thing.
Very good food, in the upscale steakhouse line.
We went there for a friend's birthday, and had some sensational food & a damn good time.

You didn't specifically mention event tickets, so I'm going to ask; Do you know about how actually playing games & doing stuff at Gen Con works?
How you get a ticket to play, when you get them, and why you need to be ready and waiting?

I have our transportation and our hotel booked. - Then you are one step ahead of the game! Great job!!!

I know I need to buy badges when they are available. - They go on sale around January. Make sure you buy them right away as this year we sold out! 

What else should I be planning for and budgeting for? - Event Registration will be sometime in May. Are you going to tell your husband before May about the trip? Or surprise him in July of next year? If you would like for him to choose his own events, he'll need to be prepared before Event Registration opens so he can create a wishlist and choose events. See this link for more details: http://www.gencon.com/experience/find

How much is parking per day? - This depends on if you'll need in/out privileges. Many of the downtown hotels charge between $25-$45 a night, but that usually comes with in/out privileges. Mall parking or other lots are usually between $20-$30 a night. Gate 10 Parking - sold by Gen Con as an event, is cheaper, but I'm not sure if that come with in/out privileges. If you're going to have to drive in every day (you're not staying downtown) - using Park Whiz or Spot Hero to book a parking spot in advance can be helpful. 

And can you recommend a nice restaurant for our anniversary night? - St. Elmo's usually gets mentioned, but Shula's in the Westin is a very pretty steakhouse. What kind of food do you like?

Piling onto Glory's reply, if you're not after fancy, but are after good, The Old Spaghetti Factory is also worth a look.

Or Buca Di Beppo if what you're after is enormous amounts of Italian food.