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I'm an engineer myself, used to work with an architect/builder/gen contractor and it is always a hassle. I think AMP hit it on the head though, where just like anything else, the designer and the customer have to work very closely.
You're totally right for having your thumb on it through the process.. if you don't, it won't only be disappointing in the end, but mistakes may be made that could be costly, both in money and time.
Have a sit-down with the architect. He has hopefully done his research and worked with whomever is going to do the construction before, so he knows what can and can't be done. Make sure he's familiar with the resort and knows what they're looking at. Are there homes on the other lots? Are they concerned about historical or architectural consistancy? Such things will put constraints on the final design.
Tell the designer what you want, absolutely. Then tell him what you'd like, but can be worked around or maybe put in later. Have him make up a few designs.. by this time he most likely uses a sophisticated CAD program and can create video "walk-throughs" and "fly-bys" of the rough design. If you're going to sink the money into a big project it is probably worth paying for his time to come up with a few concepts. If he's good he'll make some sketches and renderings as well.
Pick out what you like from each and have another sit down, start to whittle out what the final design will look like. Hopefully by that point you, the architect and the builder (and the resort) will be going in the same direction.
If nothing else I'd say expect a lot from your architect.. obviously he's working for you, and if this is a serious property he's going to take pride in making the most of the opportunity. Architects and builders use their past projects as selling points for future customers, so use that to your advantage.
One last bit of advice.. having your architect and builder together a few times will tell you about who they are, how they are going to get along. If they have never worked together before, have a few of those "sit downs" and see how they interact, if they are constructive and working to satisfy you, or trying to stroke their own egos.
I recall you saying once (about a year ago) that you didn't care what I thought, perhaps I've given you at least one thing worth thinking about here.
Hope it goes well, it would be cool to see updates as you move through the project.