Freshwater vs Saltwater boat; ASA courses
My sense is that both freshwater and saltwater has their own distinct advantages and disadvantages. Salt water is harder on the raw water side of engine (heat exchangers and exhausts), hardware and standing rigging. Freshwater is harder on fiberglass laminates. Saltwater boats tend to have been upgraded and have more frequent replacements of salt affected parts and so may actually be in better shape than a fresh water boat getting by on thirty year old fresh water cooled engine parts and deck hardware. Northern boats tend to be in better shape cosmetically but the freeze thaw cycles are hard on caulking, laminate and deck cores. Hauling out is hard on a hull. Northern boats also tend to be much more expensive.
Also with the age of the boat that you are considering on your budget, the cost of transporting (which should be way less than 5K) is still not worth it for any minimal benefit that you might obtain. A $30,000 ready to go offshore cruiser is a $15,000, 25 to 40 year old, 30-32 footer with $15,000 in new sails, and rebuilt gear. You need every dollar that you can save.
You should absolutely take the courses and get a bunch of sailing in before you buy the boat because that will shape your thinking about the boat that you choose to buy.