Great thought out points except for one flaw. The buy when you need doesn't apply to you. I run a business, the business makes me money. If I need a laptop today, I buy one today. No matter what advancements that come in technology, the waiting does not outweigh the benefit I get from getting the technology now, when I need it. If I needed an iMac when 5k was looming, the price difference is paltry in what I would earn versus waiting. That's the difference between needing it now and not needing it now.
Likewise if you are in school, work, etc. If you need it now to get your work done, waiting for what's next isn't better as your productivity suffers - and for what? A thousand dollars? The buy when you need is not utter ******** as you call it. Your philosophy is great and applies if you can afford to wait. If you have that luxury, by all means jump in at the "right" time (as you define right relating to technology). To think everyone has that luxury, is a bit unrealistic.