Good Question Jordan! Not fantasy either as most of us will spend that next 1000 before long.
I actually ask myself this very question as I survey my car each season. For some things, a 1000 goes a long way, others obviously not. But its a good figure to work with.
Right now, if I had to lock in, I'd pick:
1. Ironically, the very thing you mentioned -- new chrome trim & A-pillar trim around a new windshield.
OR
2. If I could get the same deal from our local auto resto shop, a respray and clear coat of the front end (including removing hood, painting it on both sides & fixing the bolts.) I had the back end resprayed a few years ago for 700 and it came out great.
OR
3. Rent a flatbed and head for a small town just outside Blacklick -- and drive the rest of the way!!