Don't get to the point of over-thinking every issue. A crab pot wrapped around the prop can be an issue but most boaters that have done this route seem to survive without extensive underwater gear. A close look-out where the pots are numerous will keep you clear.
Do your due diligence on the mechanical aspects of the boat. Have common sense safety items and buy tow boat insurance.
Now spend some time researching the places to go and the anchorages you want to visit. Create a menu and get a good cooler to keep the drinks cold and keep ice for those gin and tonics. Your refrig isn't that big. Get a good wheeled cart to carry home the groceries. How bout a bike or two. Don't forget to carry enough propane for your grill. A good dingy and motor with a lock and long cable will make life easier and way more fun. Pack enough tools to fix things. Bilge pump, sump pump, water pump, plumbing leaks, zinc changes, oil changes, won't all require your attention on a 2 week cruise but some probably will.
And most important; make sure the wife has enough wine.