Your advice made sense years ago; these days it does not. 2-5 year old cars with low mileage don't cost much less than brand-new models these days, unless it's some unpopular model (and they're unpopular for a good reason).
My wife's 2 year old Honda Pilot with low mileage cost ~$12k less than new. That's a hunk of change. Now, the payments were a bit higher since you don't get 0% and you don't get to stretch it out over 7 years or whatever crazy long term that they have for new cars now, but you do still save significant chunks of change buying used. If we had gone even a couple of years older, the savings to be had were over 50% versus new for cars that are reliable, popular and have >100,000 miles likely left in them.
I have to say that I'm not honestly surprised that Bennett didn't think of that conclusion, because it would require more than a strict literal interpretation of something and navel gazing, which really are his two specialties.
I was ok with the media center parts of it being worthless. I understood that they had a vision for gaming and were focused on it (although executed it poorly), and so was begrudgingly ok with the fact that they were throwing up a walled garden focused on gaming, rather than nurturing a vibrant hacker community. They killed that community, which it turns out was a lot of their customers and things withered. They really could have been a Raspberry Pi with a controller. But their controller just absolutely sucked. Their kickstarted called it "a tribute to all classic controllers out there. This will be the best controller ever." or something to that effect, which was one of the key reasons I bought it. They made it sound like they had spent some very serious effort building an awesome controller. The controller was really, really bad. If you can't play games well with the system, then it's not going to succeed.
Google does this for a reason with all of their updates in the Android store, and lots of major devs do it also. It's built into the deployment tool, where you can specify all at once or how to dole it out so that you see major bugs before they affect you're entire group. I can only assume that they have a similar mechanism that will allow it to happen simply for their custom iPad app.