@The:
Also
! Why exactly didn't nibbler hear the tone in 1999?
Nibbler was reeeally preoccupied at the time focusing on Fry… and not to mention later on in the time loop Nibbler AND Future Fry were both there being distracted by pushing Fry in. It's possible it only registered to Fry because he actually experienced that moment twice... and it was STILL subtle.
But yeah, the idea of doing THAT for 1000 years is kinda... eh.
! Was the Chauffeaur just going to blow up earth with nibbler on it? They didn't stay in contact at all? Nobody cares that the chauffeur has been blowing up planets looking for that car?
That at least they handwaved by saying he was totally oblivious to the effect he was having. Very Star Trek 4. But also kind of… meh.
@The:
Unless I missed something it seemed like a rather minor and pointless endeavor, not really a problem worth rewarding Fry for solving.
That was more of a "we kind of forcibly ruined your life by freezing you to send you to the future, and as a result you've saved the universe SEVERAL times on our behalf… and we kind of kept blanking your memory afterwards. We really do kind of owe you on that." The maguffin of the episode was inconsequential, and not was was being repaid. But the dream sequence itself kind of got Nibbler to go "You know, we really did screw this guy over a bit, and never really DID repay you back for all that..." (He promised to help Fry win Leela, but Fry pretty much did that on his own in time.)