Joe,
I basically have had a similar experience in a couple of different ways, as an apprentice, as a co-designer, and as one who engages in architectural conversation to pursue my craft with other architects. As I related on the Jay Morrish thread, having access to some great players minds has increased my knowledge exponentially, because my mentors were in the 1950's landscape architectural, practical first mode.
In one instance, I recall them crowning fairways as it was the lowest cost way to get water to drain, not realizing that it made for one very hard to hold fairway, especially after they downsized the irrigation system to meet budget, and it was typically dry.
Another architect of that era, whose course I remodeled a decade ago, drained fairways any which way to the nearest pond, even if it created a reverse slope fw that didn't hold and didn't show the fairway end very well.
And few really thought out the favorable shots such as discussed in that thread. Water on the right of a green where the wind blows left? Shallow green just over a pond on a downwind shot? What's the Big Deal? Let 'em play the course.
In some cases, greens are getting rebuilt because golfers just can't play that kind of course.
So, that generation missed the golf value a bit, IMHO. That said, after renovation of La Costa, I did get a new appreciation of how well they did the technical factors that I think have somewhat gone by the wayside in the last two decades in favor of more visuals or even more minimalism.
In reality, no architect is capable of comprehending or considering all at one time, all the factors that go into a design, and tend to rely on their few go to considerations, sometimes at the expense of others.
So, to answer George's pithy post, there is a fine line with tending to go with what you know works, and is safe, even if you MIGHT hit a home run with something different, and saying overthinking is some sort of crutch, although I think MY was thinking of GCA fans.
That said, it would be hard in a room of 100 architects and players to say exactly what "incorrect thinking" is.