Rather than derail Aruna's "The They're, there, their, your, you're, yore, loss, lose, loose, of, off, oft competition" I decided to spin off a new thread with something similar, but different:

Make sentences with successive homonyms, using at least two, preferrably three (or more?) homonyms in a row:

Because of living in days of yore, you're your own worst enemy.
I don't carry cash because it's too easy to lose loose change.
The horse could not only count to one, but could count to two, too.
Does the of work here? I'm thinking it's superfluous at best, but it's yet another example:
You're too oft off of your rocker.
I have the idea that this is something one might want to avoid in most writing, but it should make a fun prompt.