A heteronym is, of course a word which has two separate meanings, different pronunciation, but only one spelling.
Using both meanings in the same sentence is fun, but not that difficult once you've got a list - Googled - of hetronyms.

Example: "I have secret fears I would only intimate to my most intimate friends."
(Both words should be in the same language. "The clumsy waiter dropped the pate' on the customers pate." is a stretch.)

How many can be captured in a single sentence? Could be a lot; here's two in one sentence:
"I'd pay a buck or two to see the odd things a buck does when does are in heat."

Obviously there are more pairs to be discovered - how about triplets?
Could a paragraph (making reasonable sense) be written with every sentence containing heteronyms?