There's a lot of ground here, but how one decides on a builder should be sorted through a long time before you even talk about a potential project.
What is their reputation, their training, years in business? What are they known for? Are they a traditional builder or a modern one in aesthetic/tone? How does their profile dovetail with what I want to have built?
What am I looking for? I like builder X's guitar's visual aesthetic, but builder Y's tone? I want a modern guitar, but in a traditional body? These are the kinds of issues one needs to determine before having that discussion with the builder. I say I want a parlor, but all my guitars are sitka/Indian dreadnoughts -- what does this say about my likely satisfaction with that parlor guitar? What void am I trying to fill with this custom order? What do I hope this guitar will do that other instruments in my quiver do not? I want a guitar built with X material which I find very sexy but that wood doesn't do what I want out of the instrument. These are all common questions that need to get resolved, preferably before engaging the builder.
I think one of the most telling thing a builder can say is when something is out of their comfort zone and their willingness to acknowledge that there is a benefit to letting go of one's ego and saying that someone else might be a better choice because they do that more often.
The more experienced builder will likely get their tone out of whatever is thrown at them, while less experienced builders might not have the internalized database of how something outside their comfort zone might need to be addressed.
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