True, I gave a suboptimal example, in that the Air may actually be the best tool for the job. However, as you said, we can easily adjust the example so that it demonstrates a suboptimal possession with diminishing returns on improvement. For instance, take my iPhone 4S. I could buy a 5 because it is "the best," and a solid improvement on my 4S, but I have no pressing need for it. While I would benefit from a usage perspective from upgrading, I can still place plenty of implicit trust (Dustin's term) in the 4S for the ways in which I value it. By not upgrading, I can take pride in the suitability of my choices to my needs, rather than in the shininess of my devices.
Of course, that doesn't cover the pressure of choice detailed above by the "satisficers". To paraphrase Dan Gilbert (Stumbling on Happiness), adding more perfect options makes maximizers more stressed and less happy about what they do choose. Again, I prefer to place implicit trust in the quality of my selection process - its capacity to find me something good enough - rather than always in the quality of what I own. That latter threshold changes with the circumstances.