Not exactly double / reverse meanings, but there are several setences that are traditionally used to test Japanese tokenizers. Most of them are tongue twisters,

Not exactly double / reverse meanings, but there are several setences that are traditionally used to test Japanese tokenizers. Most of them are tongue twisters, like this one: すももももももももの内 "Japanese plums (sumomo) and peaches are both kinds of peaches" In speech intonation would make the word boundaries here clear, but in writing it looks odd. This isn't a tongue twister, but tokenizers often fail on it: 外国人参政権は難しい問題だ "Voting rights for foreigners is a complex problem." 外国人 (foreigner) / 参政権 (gov participation rights) is the right tokenization, but a common error is to parse it as 外国 (foreign) / 人参 (carrot) / 政権 (political power).