Todd;
I REALLY like the fact that you are even asking this question!!
So many of today's architects forget all about things like intimacy, continuity, flow, consistency, etc., and I can see from your question that you believe in building a "golf course", and not just a "collection of holes". Excellent, really.
Rees Jones's Huntsville in northeast PA has a fairly long walk across a road between the 10th and 11th holes, but it gets the routing to a property that Rees convinced the owner to purchase. On that side, there are 4 holes, and 2 of them are really excellent, another is good, and another, the last before you cross back over, is forced and strange. At that point, with only four holes left to get back to the clubhouse, the routing becomes sort of forced and inevitable. It ultimately leaves sort of a mixed reaction, leaving one to wonder if it was worth all of the trouble, necessarily.
So, my advice is to be SURE that you are going to get the most out of where you're going. If you feel comfortable that you know what you want to do, and it's just as good coming back as going out there, then I'd agree with the others here and say, go out there and build holes worth the walk!