Local nickname for the off-price retailer "Ross Dress for Less." Ross Stores is headquartered in nearby Pleasanton, CA, and also operates dd's Discounts. Since these stores offer prices even lower than the Dress for Less stores, they call them "dd's," which stands for "deep discounts." Of course this makes the name redundant (Deep Discount's Discounts).
This slang for rubber bands in Pittsburgh speak.
She-had-a-boy-again is a play on the Sheboygan's name. I heard of this recently when speaking with a friend of mine who's a Sheboygan native. As far as my friend knows, the meaning doesn't go any deeper than the phonetic relationship.
Nickname for Williamsburg, the multicultural neighborhood of Brooklyn that also happens to be a huge stronghold for NYC hipsters. When you go to Billyburg, make sure to bring a camera to get some super-ironic shots for latfh.com.
Nickname for none other than Larry Bird, native of French Lick and one of the best basketball players of all time.