Stuck in Sunset Valley School
Goggalor:
This happened in one of my hoods, with a completely different lot. It turned out that the routing over one of the lot edges had gotten corrupt somehow, and if the sims were closest to this edge they would still try to route that way and then cancel out of the action. Just like on your lot they had to be manually told to go closer to another edge to be able to get out. Very annoying that they don't try another way on their own.
I don't remember what I did about it, but I probably just bulldozed and rebuilt it.
If it is the edge problem on your lot as well, then perhaps you could try to rotate the lot once, click accept, then rotate it back and see if that heals the routing. It could be possible since rotating a lot should conform the edges to the surrounding terrain, so at least it does something to the edges.
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