Couple of suggestions for you Grillinout - and welcome! These come from a combination of my own reading of these forums, plus experience taking a road trip in my Roadster last summer (about 3300 miles up and down the West Coast).
1) It looks like you're already doing this, but get out away from home on a road trip. It can be big or small, but get away from home in a situation where you will have to charge somewhere else in order to get home. For me, that first trip was a drive from Portland, OR to Centralia, WA for lunch at Burgerville. I don't normally drive one-way 100 miles for (high quality!) fast food, but they have a Roadster specific charger and it started stretching me out. To make this trip, you'll need to plan ahead of time, using resources like Plugshare/Recargo, the Supercharger network, and others to learn where you can charge.
The point is - read all you can, but get out and DO IT
2) What I settled on from my long road trip that worked best for me, was to keep an eye on the ideal miles (rated range I believe in the Model S) reported by the car and the number of miles to destination reported by the nav. Ideal Miles - Nav Miles will provide an immediate estimate of how much battery will remain on arrival. On the road trip, I targeted ~50 miles on arrival, but was willing to let it drop to 20-30 miles (I was on vacation, and didn't feel the need to push it close to the stops). I found the difference to be very stable, especially when driving in the 50's. The estimated range in the Roadster (and it sounds like in the Model S) can vary widely based on the terrain you are traversing, and that can make it hard to tell what you have moment to moment. The Ideal - Nav though is remarkably steady.
You didn't mention one way or the other, but I'll also add that there are two different driving styles you will adopt. Your primary driving style is for when you're at home / around town. If you're like me and many others, you can't get anywhere close to 200 miles of driving in a day of going to work, errands, etc.., and your driving style becomes "ignore it". You drive, you do what you need to, you have fun driving the best car on the planet, and you plug in when you get home (easy!).
The second driving style is for road trips, and more precisely where you'll be charging away from home. I believe the Model S folks will tell you that if you're following the Supercharger network, then your behavior will be remarkably similar to how you drive at home. When you get away from the Supercharger network, you'll be making real tradeoffs between charging and covering ground. The common solution is to do your charging overnight wherever you're going, and in any case, you spend more time planning ahead, and this becomes your other driving style.
(In case it isn't obvious - the Model S comments come from my reading the forums - my experience is from driving a Roadster for a year)
Good luck out there!