If you want to see how a public event is handled at this place, try...
http://www.newenglandshakeup.com/
I attended the Shake-Up last year and was able to check out a lot of it without paying the admission.

I'll be thinking about what I can do to help with the Pinball Event. I've helped the Pinball Expo since their first year,
but there's more I could do for an event that's within a nearby drive.
.................David Marston
(Co-founder of New England PinFest, which ran 1991-1995)

For those bringing games for the free play area: you can show up as early as 7:00 AM either Friday or Saturday! To my mind, that's another great incentive for bringing a game. You can hang out in the free play area after setting up your games, but everybody has to cooperate for efficient, orderly, and SAFE setup.

I am told that every game in the free play room will need a card. Among other things, the card will indicate whether the game is for sale. Every game is automatically entered in the Best In Show contest, and the card is used to determine who gets the prize.
.................David Marston

I've been to this hotel for the New England Shake-Up! and I feel confident that they can handle Pintastic.
.................David Marston

For Friday or Saturday setup, you need to come to the registration area and get your wristband and "game cards". We may have a separate registration table for the free-play area Friday morning (7:00-10:00) IF we have enough volunteers to staff it. If you come in Thursday for setup, no wristbands are used, but there will be a "game card" for each game.
.................David Marston

In practical terms, the Brimfield weeks are pretty much impossible. (Brimfield is the next town West of Sturbridge.) Check out the aerial photo on the brimfield.com home page. These events drive up hotel rates in a 60-mile radius!

Early August might be better, on a weekend adjacent to ReplayFX.

I agree about conflicts. I think the best we can hope for is no conflicts with gamer-cons on two levels. (1) No conflicts with any "worldwide" show that has pinball (NW Pinball Show, ReplayFX, Pinball Expo), and (2) avoid conflicts with regional shows based on arcade/coin-op content and the radius from which the show draws. As an example of (2), Louisville Arcade Expo has a lot of pinball content and draws from Pennsylvania and Virginia, as does Pintastic. There isn't much chance of the dates conflicting; I just chose that example for its geography. I think it's OK to have the Southern-Fried Gameroom Expo (Georgia) and the Rocky Mountain Pinball Showdown (Colorado) on the same weekend as each other, but there could be issues with SFGE and Pintastic on the same weekend.
.................David Marston

I'm not sure what more there is to offer. The free admission (or admission rebate for VIP badges) applies separately to each day. Anyone who can come only for Saturday would have that incentive, plus they'd get into the free-play area early on Saturday, and they would have a ticket in the thank-you raffle.

For 2016, we will want to show the hotel that we can generate even more room-nights for them, which means we want to get people to attend for multiple days and stay over. But for those who live within driving distance and would go home each night anyway, I hope they would take a look at the fill of the free-play area as they leave on the first day, and if they see a hole, consider bringing a game for the second day to fill that hole. Does anyone have any further suggestions?
.................David Marston

One thing that would start very soon is having volunteers to bring publicity materials to similar or related events. For example, if we had cards printed and ready, we would have asked for a person who was attending the Cleveland Pinball Show to bring cards there and set them out for people to pick up. The same idea applies to tournaments, pinball parties, gamer-cons, etc. Such efforts will probably be coordinated through email and the Pintastic website.
.................David Marston