We are actually in a 'chip-punk' version of the past in which silicon based computers became available all the way back in the late 20th century. The original Eliezer made friendly AI with vacuum tubes.

1. No if they are in a historical simulation. The real architects of the Singularity weren't billionaires.
2. No if they are in some kind of holo-game, for the same reason that people playing computer games don't hack them to make their character level infinity and impervious to bullets. Where would be the fun in that?

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.