I was lucky to get in and out of this hobby, as far as owning three machines goes, and broke even. Along the way I learned A LOT and that was great. I will tell you this from my experience and I am sure others have had the same: buying the machines was the easy part. You brought cash and laid it on the glass. However, selling is a whole new dimension. Tire kickers, low ballers, people who think you will be there to fix the machine after they buy it, etc. I firmly believe the youth of today are not into buying a giant piece of noisy furniture. There's a reason today's kids love "apps". However, I kept my Crystal Castles and my kids still play that machine but it's an awfully large one trick pony. After 4 years of owning pins, my kids never took to them. But you can bet Microsoft Points are a huge hit as birthday presents.
Bottom line, buy what you like. All this talk of "they ain't building any more of them" may be true but the market may not be there for when the time comes for you to, gasp, SELL.
Me? I would like to get a nice EM in the future. But not right now.