I think this is kind of missing the "if it's inadequate" clause of the heuristic. In your example, the painful boots were clearly inadequate, and by the heuristic, it was time to upgrade to the best equipment you could afford ;)
Skiing does make for some examples of a couple weaknesses in the heuristic, though:
First the "best equipment you can afford" part is pretty poorly defined. Suitability of ski equipment is contingent on the skill of the skier and the type of skiing, so you can't just pick the most expensive thing and expect it to be the best for you. Skis are especially nasty in this regard in that the most expensive equipment often makes performance trade-offs that are actively hostile to beginners or use in the wrong conditions.
Additionally, ski equipment is consumable (at least in the hands of an aggressive skiier), which largely invalidates the cost-optimization rationale of the heuristic.
Skiing probably wants a somewhat modified heuristic, along the lines of "Start with the cheapest tool, use it until it wears our or you find an intolerable problem, and then choose a replacement that solves the problems with the previous iteration."
Skiing does make for some examples of a couple weaknesses in the heuristic, though:
First the "best equipment you can afford" part is pretty poorly defined. Suitability of ski equipment is contingent on the skill of the skier and the type of skiing, so you can't just pick the most expensive thing and expect it to be the best for you. Skis are especially nasty in this regard in that the most expensive equipment often makes performance trade-offs that are actively hostile to beginners or use in the wrong conditions.
Additionally, ski equipment is consumable (at least in the hands of an aggressive skiier), which largely invalidates the cost-optimization rationale of the heuristic.
Skiing probably wants a somewhat modified heuristic, along the lines of "Start with the cheapest tool, use it until it wears our or you find an intolerable problem, and then choose a replacement that solves the problems with the previous iteration."