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Well. If one (Omega or someone like him) asked me to choose between 1000 years compressed into the next hour or just 100 years uncompressed inside the real time from now on ... I am not sure what to say to him.
Again, the existence of other people complicates this (as it does so many other things). If I'm offered this deal right now and choose to have 1000 years of subjective experience compressed into the next hour and then die, then e.g. I never get to see my daughter grow up, I leave my wife a widow and my child an orphan, I never see any of my friends again, etc. It would be nice to have a thousand years of experiences, but it's far from clear that the benefits outweigh the costs.
This doesn't seem to apply in the case of, e.g., a whole civilization choosing whether or not to go digital, and it would apply differently if this sort of decision were commonplace.