Timing is everything. There's early adopters and bleeding edge adopters. The Model S is the "bet the company" product. And people buying the Model S in the first 9 months are bleeding edge. People buying now are taking a real risk although I think it's good one. People buying 9 months now should have a much clearer view into the crystal ball.
Viability: In 9 months, we should know if Telsa can ramp production. We'll also know a lot more about the Model S (extended reviews and quality) and should have some insight into whether the demand will sustain itself. Given all that, we should be able to guage whether Tesla will survive in the short-run (a year or two) and have some insight into their odds of surviving in the long run. It looks like Telsa can be profitable if the Model S does even reasonably well. So as long as they manage the financials so that future vehicles don't turn into "bet the company" investments, things should be ok for at least a few years.
Quality: In 9 months, we should know about most if not all the serious bugs that don't show up until you scale up production including stuff that triggers recalls.
Obsolescence: the question is will market forces and technology trends will drive the cost of a Model-S-like car down to the point where the S has near zero resale value? Think computers.
This is where it gets complicated because you've got market forces, technology trends and have to think mid-term (2-3 years) and long-term. Long-term is all about technology trends. Short/mid-term is all about competition (market forces).
From a competitive standpoint, I don't think anyone is going to bring a Model S-like car out in 2-3 years at competitive prices. They can't do it without battery management tech like Telsa has. And if they had that, we'd be hearing about it.
From a technology trends standpoint, the major thing that can change in EV-space is battery and battery management technology (charging, etc.).
What is very very unlikely to change significantly is the chassis design fundamentals, manufacturing with aluminum, electric motor technology, brakes, tires, wheels, etc. In other words, almost everything else about the car.
Elon says that battery density is improving at 7% a year. In 5 years, that means batteries will be 40% more energy-dense than they are today. So 5 years from now, I'm expecting that EVs will have 40% more range at today's cost. In 3 years, that number would be 23%.
That doesn't sound like a game-changer to me. It should cause Model S to lose some of its value faster than normal. On the other hand, the Model S could hold value better than normal because of the fewer # of moving parts that can wear out. Who knows? Take your best guess.
However, the 40KwH model will be most vulnerable to this over the next 3 years because a 23% increase in battery density could increase the range of non-Tesla EV's to be roughly comparable to the Model S. But I don't see anyone matching the range of the 85KwH model in <3 years. Except Tesla. And I expect Tesla will use the density improvements to drive cost down on the GenIII first before they increase range above the current Model S. But again, who knows? That all depends on how successful Tesla is at holding down costs everywhere else in the GenIII.
How well will the Model S hold value over 5 years? Beats me. The car itself will not be obsolete. The battery tech could be outdated enough to drive value down. On the other hand, if Tesla is still around and viable, a Model S owner (or used car buyer) could just wait until batteries get "cheap enough" and buy a new pack. That gives you an N year car with battery density and cost to the new cars at that time. With far fewer mechanical systems that are aging and have to be repaired/replaced. Not as good as new but lots better than buying say, an 8 year old conventional car.
The tech trend that could wipe out Tesla's current technology advantage is if future batteries don't need significant management. Or someone develops another compelling power source for cars. We're probably at least 5 years away from that assuming it ever happens at all. And if Tesla is still around when that happens, hopefully they'll have developed enough other advantages that they can stay in business.
Summary: if you're locking in now, yes, you're a bleeding edge adopter taking a significant risk. That's why you have the option of choosing "Signature Red"

. If you can wait a while longer (or have no choice because you have a >9000 P#), you'll still be an early adopter but I think we'll have a pretty good view into what kind of car the Model S truly is and Tesla's viability over the next few years.
Disclaimer: in addition to being in line for a Model S, after I did the above analysis and thought hard about Elon's track record, I went long on Tesla.