I've been burned repeatedly by your philosophy. It only seems to hold if you know exactly what you want. I've got closets littered with high quality things that I don't ever use anymore because I lost interest before I could ever appreciate its quality.
Selling them is a pain of its own. I would have preferred to have bought cheap and not have to worry about recuperating value.
I think people get it into their heads that they need to be a buy cheap or buy quality person entirely, and I think the most succinct point I could make is that it doesn't have to be one extreme or the other. Buy quality for the things where you know what you want and value the quality improvement, and buy cheap for the things that are new and unknown to you. You don't need a pro-quality snowboard before you decide that you like snowboarding.
