Greg, yours is a good question. I get it. I wrassle with these thoughts all the time.
I get a sense that the newer breed of collector is looking for art, for a story, for historic relevance, attention to detail, highest quality.
As far as judging at Dixon's, for example, I take this as a guide. One can learn a heck of a lot by entering a gun into such a judged event. Do not use the judgement as a mandate how you have to build for the rest of your life, but as a guide to improving your skills.
If you want to emulate 18th Century work, for example, study originals in museums and private collections where available.
If you want to follow the more contemporary track, seek out builders in the style you like. Go to gun shows, talk with these builders.
Don't accidentally use 21st Century ideals to build 18th Century arms.