See the one-dollar words page for what $1 words are. Basically, if we let a = 1¢, b = 2¢, ..., z = 26¢, we can sum up the letters in a word. If we do this, we will find several words that sum to $1.
So, you could try stringing together $1 words to form $1 sentences, sentences where each word has a value of $1. One such sentence might be: "Prevent strains." A longer sentence might be: "Therefore, obscenely twisted conniver imported thirty chromium stoves, collecting delivery surcharge." I bet no-one's ever said that sentence before!
Try creating your own $1 sentences. You could try creating one that's even longer than that one, or you could try to create a sentence that's more meaningful than the one above, or use some other criterion to create the "best" sentence.
Alternately, you could choose some other value (say, 87¢, or $1.18, or something else) and create sentences where all of the words have that value. See what the longest sentence you can find is where each word has the same value, no matter what that value is.
You may find this list of $1 words to be useful. You may also be interested in a $1 word calculator or a few $1 puzzles and problems.