I would echo some of Marks comments and add that of any time it would probably be now with the capabilities of both pipelines and formula queries. In my opinion if you start off with a well defined catalog / template where your rules are in place via relationships of what items are 'suggested' or required to go with what, when it comes time to apply that to an actual quote, you can leverage a lot of these tools to (1) use summaries/formula queries against the template to determine if you've got everything you need or (2) leverage those same things to just create/fill in the gaps for the end user.
My suggestion would be to figure out how you would build the configuration template the rules that will apply in each type of circumstance and then engineer that in a way that when you actually apply it to a quote then it should easily fall into place. The legwork would be getting all of those configuration pieces ready to go.
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Chayce Duncan
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