Don't worry, I totally understand your point of view.
The short answer is: no. Unfortunately.
But the question is perhaps not the most convenient. The problem is not the trust on true/false. The answer is actually false, the Nspire got that right. The problem is you cannot, on floating point arithmetic with fixed precision, trust on = comparisons.
Every single comparison must have a specified tolerance level. = is exactly that. =. One cannot set = to mean "approximately equal to". And with decimal numbers every comparison should be an "approximately equal to". Meaning that you should look at the difference between two numbers and rely on intuition/knowledge to decide whether those two numbers should be considered equivalent or not (example: I have a bunch of programs that, depending on the conditions of the problem, set a tolerance of 10^-8, others set it at 10^-10 and others at 10^-5).
Back to the question in hand...
We have 14 digits of precision. Division doesn't lose precision, therefore the error is maximized by 10^-13 (if we're dividing small things by small things - see below)
But a power of a fraction, being computed as the power of an approximation, will have a larger error.
The sine of a fraction, being computed as a power series expansion of some sort will have a larger error...
Each and every single operation you do will have a different error, either of the magnitude of the precision or bigger. Good algorithms have errors that increase slowly with the loss of precision of the inputs, but no algorithm exists that, in general, can assure that precision will remain the same. And in some cases the best algorithms available (btw, the first person to suggest that better algorithms must be found will get a list of PhD positions in numerical analysis as a reply) may ensure that you "only" lose half of the initial precision, meaning that if data has 14 digits of precision the output will have a whooping 7.
Because of this, the Nspire only displays 12 digits. To account for errors 1 or 2 orders of magnitude larger than the machine precision. Older TI graphing models had 10 digits visible but only 11 internal, which caused more numerical approximation errors to be visible; If memory serves me right, here's the full list:
TI-80, TI-81, TI-82: 10 displayed, 11 internal
TI-83, TI-83+, TI-84+: 10 displayed, 12 internal (not sure whether the 83 didn't have only 11 internal)
TI-85, TI-86: 12 displayed, 14 internal
TI-89, TI-92, Voyage 200: arbitrary precision; 12 displayed, 14 internal in floating point.
TI-Nspire: 12 displayed, 14 internal
TI-Nspire CAS: same as 89, 92 and V 200
(can anybody confirm this? I'm not in my twenties anymore, memory for this kind of details sometimes fails me)
Again, back to the question in hand...
A numeric derivative of a "simple" function like sine, cosine, exponencial, will have a typical precision or, perhaps 8, 9 or 10 digits;
Numeric derivatives of tan(x) or ln(x) or rational functions will have a precision that depends on where are we computing it (degrades rapidly near discontinuity points).
Higher order derivatives behave worse and worse as order increases (and by worse I mean that if 1st order derivative loses 2 digits in precision, 4th order will lose 8!);
Taylor series are the worst when computed numerically because each term requires a higher order derivative, plus division by really large numbers!
Numerical integrals typically lose 2 or 3 orders of magnitude in precision, and can be worse when integrating "nasty" things.
And, to make matters worse, we have 14 digits, not 14 decimal places. Meaning that a numeric value of the order of 10^7 will have a precision of 10^-7. And the precision of the result is at best equal to the worst precision of the input.
So, the answer is no, it cannot be done (except by considering more and more cases into some "exceptional" behaviour and next time we'll be discussing questionable accuracy for other mathematical operations; and even so, those exception can be dangerously close to what may be considered CAS!).
There's no way the TI-Nspire can decide when to consider two numbers close enough as equal or not. Plus, if one was to consider a=b if |a-b|<10^-13, for example, then Pi=3.1415926535898 should be considered equal to 3.1415926535899.
Meaning that to the question Pi=3.1415926535899 the answer should be true (and it's obviously false). But by the same reasoning, 3.1415926535899=3.1415926535900 should also be true (and, again, it's false). By transitivity, Pi=3.1415926535900 should be true.
And, (ah, la pièce de résistance), proceeding recursively, one could make the Nspire return true to the quesstion Pi=4. Which, by the way, could have been passed into law in the state of Indiana in the 1890s, but fortunately wasn't. ;)
I hope this helps clarifying things a bit.
Cheers,