Collin,
No offense, your TheMightyHobie18 is definately the nicest one I've ever seen. No matter what, in the end, it will still be a TheMightyHobie18. You gotta decide what you REALLY want that boat to do and how much it will end up costing. You're already pretty close if not past what a good used F18 would cost you. I've sailed around you at the Dike when you were reaching with the wings on it. Your boat speed was about the same as mine for that run. It's a good and fast 18. You may get a couple more degrees going to weather but at what price?
If you give a pig a nose job, you'll still end up with pork chops instead of prime rib.