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Ann Arbor, MI
Moe
Mid 1996, not sure of the actual date. The Addams Family and I still have it.
Built our game room in the winter of 2009. Our plains were to fill it up with classic arcade games from the eighties . The game room was a Harley Davidson theme and bought everything that we could find that was Harley. I remembered seeing a Harley pinball machine at a Harley dealer and went on a search to find one for our game room. Found a HUO Harley Davidson 3rd Edition to go along with everything else and this was the only pinball machine that I was planing to put in there, the rest were going to be arcades. Ten years later , I have 20 pinball machines and only a small collection of arcades.
7/12/11 STTNG for $1500 off Craigslist
March 2016, Bally Kick-Off, $300 off Craigslist. We drove from metro Detroit to a place near Goshen, IN. I didn’t know about the Jones plugs, so I unbolted but didn’t completely remove the head because I didn’t want to stress the connecting wires. To let it fit like that in my Ford Escape, my poor wife rode all the way back with her seat shifted fully forward and unreclined all the way. She got a sore back, and wasn’t happy when, after we got back I said, “Look, Honey, the wires can be disconnected!”
Breda
Edmonton, AB
Gottlieb Miss Annabelle a 1959 single player woodrail. This was the first pinball I ever saw or touched. It was in the basement of a coworker of my father. Played it for three hours on that first of many visits. When my fathers company moved us across the country the game was given to me as a gift. The pin sits in my home office. I have had Miss Annabelle since 1966 or 53 years if my math is correct. Over the years I have had well over 500 pins. My current inventory is around 225. Thanks to Miss Annabelle I have had a long happy addiction to our wonderful hobby. Merry Christmas
....wait I was born that year... 
Lempäälä
9/19/2016 I bought a Buck Rogers for $750 from someone on Pinside, had a new all-in-one board and was in nice condition. I had eight total by the end of that year and just hauled my 74th total machine down to my basement. I have hauled 66 of them back up the stairs when I sold them.
First one was around 1979 . Way before computers . You had to look for them in want adds in a news paper ! Picked up a Spirit of 76 along with a em gun game called Pony Express . I think I payed $350. ea. for them . Only place to get parts was Wico or to stop in to a local vending place .
December 14, 2001. Last Action Hero. $1210.70. From Wes Pinball. His house was full of pins. I remember he had TZ and TAF.
I should have been buying all his great pins then. I was new to the hobby and did not know enough to scoop them up.
Still have LAH.
October 1994 Fireball Classic. Hired Colonial Amusements to replace power supply, shopped it myself through trial and error.
Allowed back glass to fade through ignorance. Sold it for what I paid. Now have a nicer one.
First game Dec 25, 1970. Bally Trio. $75
Fully working, Christmas gift. Imagine my surprise! Never forget it....
Paid $180 for a 1964 Ski Club at an auction almost eight years ago. What a boring game, but after that I realized that you could actually have pinball machines in your house. A week later I purchased a non-working Speak Easy at a garage sale for $200. After getting that machine in good working order the addiction took over.
Immediately after that, I agreed w/ my wife to only have a max of three pinball machines in the house. I tried to sneak a forth machine in but was quickly reminded on our agreement. I did sell that forth machine but used that money to buy a Merit Touchscreen. She never stated that I couldn't have an arcade machine, so that's what I did.
Fast forward > As of now, we have an arcade room in the front of the house & my meager collection of three pinball machines in the back room. We have had 60+ pinball & arcade machines that have come & gone, but that's part of the fun. My wife & I have some fierce competition on the arcade machines (Golden T, Multicade, Touchsceens, etc.) but we cherish our pinball machines.
Yesterday we had talked about going to movies. My wife stated that she would much rather stay home & play the machines. So we stayed up all night playing JP3 till 4:00 AM. You can't beat that for a cheap date. Love this hobby!
High Speed, 1994. Paid $500, very nice condition. Sold 5 years later.
Twilight Zone, 1999. Paid $800 at an estate sale, ad for the sale was in the newspaper, starting at 10am on a Sunday. Just by luck it was the first item up for auction. About 50 people attended, Bid opened at $800, and that was the hammer price. Another pinhead arrived at 10:15am looking to purchase, I was already loading it up. Machine had just been sitting in the family room for 5 years, beautiful condition, Still in my collection.
Firepower, the "gateway drug" of pinball machines, in April 2013. Really wish I'd gotten into the hobby about ten years before that.
1st purchase. I sold my Ibanez bass guitar so my dad and I could buy a Solar Fire in 1992 for $400. I was 14. Had it for a few years and sold it to buy a mountain bike in 1996.
1st purchase second go around was a Black Knight in 2015 for $1300.
My wife and I used to play pinball when we were dating back in high school so we treated ourselves to a pin on our 20th wedding anniversary. The date was 07/2009 and the game was Scared Stiff. Paid $2700 for it back then.
Bought an Elvira & the Party Monsters at the TX Pinball Festival in October 2003 for $1200. Sold it to upgrade to Theatre of Magic. Got another EATPM 4 years ago, before selling it again. Have owned 9 different pins over the past 16 years.
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