>Some might sound a bit yoda-ish

Absolutely. But I was just thinking there are some sets of words that are grammatical in almost every possible order. Best approach would be to think of words that are homographs of other words and have lots of meanings.

This is not the best example of that, but...

It will say “you”.
“It”, you say, Will?
It? Say “Will”, you!
Will it say “you”?
Will you say it?
“Will it”, you say?
Say it, will you?
Say you will it!
You say it, Will.
You say it will.

etc.

What is the longest set of words with the most permutations?