eco5280, have you researched how available those superchargers really are? Just my personal experience, I work very close to the Hawthorne supercharger here in Los Angeles and I can tell you that many of the times I drive by, it seems like all the charging stalls are occupied.
Just like you, I'm stretching to buy a 60 and even an additional 2000 bucks is a bit too much for my budget and I'm debating if it is worth it. If I'm spending that money, I certainly don't want to get there and then have to wait for other people to finish charging. I know they are adding more superchargers but, as more Teslas are being sold, I wonder if the supercharger network can keep up with the new users. I would be interested to see if others have had any problems using the superchargers.
Also, I personally don't like to take my own car on a long road trip, especially a very expensive car. Road trips put a lot of wear and tear on vehicles. I usually prefer to rent a car and if something goes wrong with the car or I get in an accident, I just call the car rental company and they take care of it.
Don't get me wrong, I love the Model S but I'm also a practical person, I commute 100 miles each day so driving my tesla would be perfect but I don't have to necessarily take it on road trips. Also, my wife will keep her car so we could use hers for long trips if need be. That is just my personal opinion but I totally understand where you are coming from. Anyway, you are going to love your Tesla with or without the supercharger option. Good luck with your decision!!