Once the Adult Education Annex is up, and Lenny goes there to teach (while Carl dates his sister), it’s all downhill for Lenny: he no longer has Carl and things get very bad indeed. If you want to see what brought about Lenny’s terrible decline, take a look at what happened in the Buddha’s Got Back (the first level 27 quest) here.

So let’s follow Lenny on his downward spiral:

1. Lenny’s Downfall Part 1 It’s only when Lenny finishes teaching at the Adult Education Annex that he remembers that his fallback teaching job is unpaid. Luckily, he has a fallback fallback job – being a best-selling mystery novelist. So, Lenny goes to work on his mystery novel (12 hours).

2. Lenny’s Downfall Part 2 After 12 solid hours working on a single paragraph, Lenny’s in the mood for a beer. But without money and without a friend, there’s no point going to Moe’s. While he can’t just sit around feeling sorry for himself, he can walk around and feel sorry for himself. So, Lenny wanders aimlessly around town, moping (24 hours – keep Chief Wiggum free as he finishes, to be safe).
3. Lenny’s Downfall Part 3 Chief Wiggum feels like doing his job, or something resembling it. Apparently, while moping, Lenny has committed a number of offences. And that means that Lenny needs to go to the Police Station for questioning (8 hours – keep Mayor Quimby free as he finishes).

4. Lenny’s Downfall Part 4 Now it’s Mayor Quimby’s turn to step up:

Mayor Quimby: First question. Have you ever donated to my campaign?
Lenny: No. I don’t have a job or any money.
Mayor Quimby: That’s terrible. But at least I can offer you a place to eat and rest.
And off Lenny goes to Springfield Penitentiary (24 hours – keep Mr. Burns and Carl free as he finishes)

And there we leave Lenny. At least in my town he has a nice view of Mount Carlmore.

The level 27 walkthroughs will continue…