So Eleanor's memory got erased and the "Good" Place rebooted, so she wakes up again seeing a slightly different welcoming sign. How do we know this has been the first time this has happened? Maybe her memory (and the other three) has been wiped out and the "Good" Place rebooted several times, everytime they figure things out.
shareWell Michael mentioned this was the first time to his boss. So the first season was the first time.
However its possible the Eleanor we left with isn't the second attempt.
Did he say it in front Eleanor & Co.? In that case, he could have been lying.
shareHe could have been lying but he didn't seem to care about telling them everything at that point so I don't see why he would have.
shareExactly, he looked too carefree about that.
The point is: now that the twist has happened, we shouldn't trust him at all from now on.
The Judge character and Michael were alone, (when they gave time for the group to decide who is going to the Bad Place) and the Judge told Michael something like "remember what I told you before this all began? You'd be lucky if it worked six months."
He didn't say anything like "why do you insist on trying again and again." The dialogue supports the fact that this was the first attempt. And again, when it's just Michael and the Judge and Michael is begging for permission to reboot, (while Eleanor is writing the note to hide in Janet) the Judge warns him that he gets one more try to make it work.
All the evidence supports that it's only been one attempt and that the reboot we see is the second attempt.
"The plastic tips at the end of shoelaces are called aglets. Their true purpose is sinister."
We know it's the first time because not only did Michael and the judge talked about it, but when Michael confesses to Elanor about the whole thing he is really surprised she found out.
Why? What would be the point in lying if he wipes her memory anyway?