Not really. Think of Nozick's experience machine. If you were to use the machine to simulate yourself in a situation extremely close to the center of the singularity, would you also give yourself the looks of Brad Pitt and the wealth of Bill Gates?
a) Would this not make the experience feel so 'unreal' that your simulated self would have trouble believing it's not a simulation, and therefore not enjoy the simulation at all? In constructing the simulation, you need to define how many positive attributes you can give your simulated self before it realizes that its situation is so improbable that it must be a simulation. I'd use caution and not make my simulated self too 'lucky.'
b) More importantly, you may believe that a) doesn't apply, and that your simulated self would take the blue pill, and willingly choose to continue to live in the simulation. Even then, having great looks and great wealth would probably distract you from creating the singularity. All I'd care about is the singularity, and I'd design the simulation so that I have a comfortable, not too distracting life that would allow me to focus maximally on the singularity, and nothing else.
I agree these are possibilities. However, it seems to me that if you're going to use improbable good fortune in some areas as evidence for being in a holodeck, it only makes sense to use misfortune (or at least lack of optimization, or below-averageness) in other areas as evidence against it. It doesn't sit well with me to write off every shortcoming as an intentional contrivance to make the simulation more "real" for you, or to give you additional challenges. Of course, we're only talking a priori probability here; if, say, Eliezer directly catalyzed the Singularity and found himself historically renowned, the odds would have to go way up.
In passing, I said:
And lo, CronoDAS said:
To which I replied:
There's a certain resemblance here - though not an actual analogy - to the strange position your friend ends up in, after you test the Quantum Theory of Immortality.
For those unfamiliar with QTI, it's a simple simultaneous test of many-worlds plus a particular interpretation of anthropic observer-selection effects: You put a gun to your head and wire up the trigger to a quantum coinflipper. After flipping a million coins, if the gun still hasn't gone off, you can be pretty sure of the simultaneous truth of MWI+QTI.
But what is your watching friend supposed to think? Though his predicament is perfectly predictable to you - that is, you expected before starting the experiment to see his confusion - from his perspective it is just a pure 100% unexplained miracle. What you have reason to believe and what he has reason to believe would now seem separated by an uncrossable gap, which no amount of explanation can bridge. This is the main plausible exception I know to Aumann's Agreement Theorem.
Pity those poor folk who actually win the lottery! If the hypothesis "this world is a holodeck" is normatively assigned a calibrated confidence well above 10-8, the lottery winner now has incommunicable good reason to believe they are in a holodeck. (I.e. to believe that the universe is such that most conscious observers observe ridiculously improbable positive events.)
It's a sad situation to be in - but don't worry: it will always happen to someone else, not you.