Dauntless: I'm going to buck the trend and recommend against the windlass for now. Here's why: Your intended use pattern will likely not include that much anchoring out. Like you apparently will, we use our Dory primarily to get from Anacortes to Decatur, and also day trips, fishing, whale watching, etc. Moored/trailer stored in Anacortes, and on the hook at Decatur. I hate to say it, but you'll also use the stove, sink and berths a lot less than you think. The reason is you have your cabin as a primary destination. I firmly believe in having excellent ground tackle installed and available, but we've gone 5 years with the C-Dory and never used the anchor once! In our case a windlass would likely have failed due to lack of use, and complicated an emergency deployment. Our use pattern is why we went from a Cruiser to an Angler last year. Cockpit storage to haul gear and for crabbing is much more important than a kitchen/dinette berth for us. We got our 2007 Angler with standard top, twin Honda 40's, Hummingbird GPS/Sonar combo, Standard Horizon DSC VHF, 2 Scotty electric downriggers (the Scotty mount/plug will accommodate an Atlas pot puller - $500), a robust Delta fast set anchor/ground tackle setup, and a new tandemEZ Loader trailer complete for right at $45K from EQ, who unfortunately doesn't sell C-Dory anymore. Electric wipers and hydraulic steering came standard with the boat. I don't question your Cruiser selection, however, since they're easier to market if you ever choose to sell, and are obviously more liveable if you do get into extended overnight cruising. I just didn't want to pay extra for things I knew we wouldn't use. I would also recommend choosing one of the integrated/expandable electronics packages so you could add radar, engine monitors, etc. as time goes on. I wanted to pay cash so I had to hold the line on the extras. I will therefore need to add a stand-alone radar unit when the time comes. Best of luck with all of this. Rigging a boat is a very fun process. See you later on Decatur! Mike.