Alex,
As someone who has never had a caddie I guess I'm not best placed to answer your question - that said, unless it was absolutely necessary to have a caddie i.e you couldn't play without one, I don't think I would use one.
Unless.
He or she was prepared to just carry the bag.
One of the fundamental parts of the game - to me anyhow - is the thought processes used to play and hopefully beat the course. These thought processes change depending on numerous variables, the hole and its design, weather and to a large extent; me.
I know you suggested that skill or handicap should not be a factor but surely the two go together; thus, strategy awareness cannot really be considered unless you are aware of your own ability. That's not to say, as in your example, an average golfer cannot also be capable of understanding strategic design - it's just that even if you can read and understand the architects intent, ultimately how you play the hole depends on you.
As an aside - nothing beats playing well around a course you know nothing of - using just what you see and the odd sprint up a dune or two to see what is laid out before you. Having a caddie tell me would ruin that aspect, for me anyway.
Neil.