I love the story Ken, and I think that the brief descriptions of the helicopters provides the perfect exception to the phographic metaphor. i.e. You used Boeing-Vertol because you had the need and the knowledge to maximize its purposes. If you had been attempting to use a Schweizer 300 or (God forbid) a Robinson 22, you never would have gotten what needed to be done accomplished. But, you no doubt put in countless hours in similar small helicopters to get to the point where you could safely manage, and maximize the use of, larger birds. No one first learns in a Boeing Vertol, it just wouldn't make sense.
On the bike, if one doesn't have the need or the ablility, the nicer bike isn't going to matter in the least; but, there are the rare one's among us who can justify the expense, and prove their worthiness.
Of course, I enjoyed my time in my friends Bell 206 quite a bit more than in his 300C. And since the cost difference is far narrower in the cycling world, if the nicer bike means you'll ride more, then by all means get the bike that you'll actually want to ride.