Whatever you think of adding WiFi tech or not for multi-player games, my main concern would be actual competitors online at any given time to play against one another. I equate it to two recent flights I took. One was several hours from Texas to Maui and then back again, while the other was a quick 3 hour flight from Texas to Las Vegas. All of my flights had individual entertainment systems for each passenger that were free to use. I was excited thinking that I would be able to pass time by playing some competitive games with other passengers (e.g. poker, trivia, etc.) Between all of the flights, I literally started dozens of games throughout the flights and waited several minutes most times, but not a single time did I see a single other passenger in any of the game rooms. In these instances, there was a captive audience of hundreds of people with limited entertainment available, yet I was never able to coordinate a game with a single one of them.
I don't know what the install base is of a given pinball title these days, but I don't imaging it is more that in the low 1000's. I can't imagine the coincidence it would take for just two random home owners of a particular pin title who were in the subset of owners who even cared about online play to be online looking for a game at the same time. There may very well be other applications for a connected pinball machine, but if you look at things from a business' perspective, there is little to no reason why they would/should implement such technology for the purpose of live online competition as the userbase is just not there to financially support such a "feature". Looking at it from the opposite perspective, I don't think manufacturers lose a single sell because a pin does not have head-to-head game play capability.
Just because you can doesn't always mean you should (suddenly a Dr. Ian Malcolm quote I have on my PinSound Jurassic Park orchestration comes to mind). My thought would be that if such a demand was there, then why doesn't a third party invent/implement such a capability? Without oversimplifying the tech required, I'm sure that if a profit was to be made some pinhead entrepreneur would already be in the process of developing the technology.