Quoted from mbaumle:

Since I'm not someone who'd buy NIB, I just play what I can find on location. Given that, I don't think I've ever really had a bad time playing a newer Stern game. In some locations where they'd have a mixture of 90s B/W games and new Sterns, the Sterns almost always play better (just because they're newer).
But then there are the rules. I can usually progress pretty deeply in the rules of a 90s B/W game on a regular basis these days--especially in arcades where the pf isn't smooth waxed and lightning fast. So if I play a game or two, I usually find myself exploring most of the games features and accumulate a replay or two, then I get bored and hand the replays to the kid behind me. On a Stern game, I almost NEVER get deep enough into the rules to max it out, so I find myself playing them more than I'd play a B/W. I see many people expressing the same thoughts when they have them in their collections: Deeper ruled Sterns hold people's attention much longer than the shallower rules of past.

Quoted from PopBumperPete:

Because new games are new.
The last of the BW games came out almost 20 years ago

Quoted from IdahoRealtor:

Yep. Or ACDC, or Tron, or The Walking Dead, or Ghostbusters, or Game of Thrones. Sterns are not all long-playing. I think someone just needs a bit more exposure.
Sterns appeal to me on many levels.
Considering the better 90s pins are commanding $3000-$6000, and considering the cost of parts and restoration, $4995 for a NIB Stern shipped to my door is very appealing.
I prefer playing over dealing with repairs and breakdowns.
I prefer calling my distributor, or picking up a lightly used Stern locally, than having to wait and scower and drive great distances in hopes of finding the title I want in good condition for a fair price. The "fair price" part is becoming increasingly difficult.
I like newer, brighter, faster, better sound quality, and more depth.
I find many of the new Sterns to be more exciting and more adrenaline pumping than the 90s pins.
I find Sterns to be highly reliable and generally easy to service.
I like that Stern is still in business and lifetime free tech support is a phone call away. And the warranty can come in handy.
New Sterns earn better.
There's more reasons, but that's enough for now.
And for what it's worth I do enjoy older pins and have a deep appreciation for them.