I sailed an Endeavor 47 ketch all around SW Florida, Dry Tortugas, Key West and all over the Bahamas for several years. I think most Endeavors in the Florida area were sold by Russell Wakefield, who is long out of the business and retired. The 5' keel won't be a problem. When you are going to spend a lot of time on board a boat, you have to look more deeply into it than what has been discussed above. You have to think about longer distant cruising and living on board. So, you need living space, places to stow items that aren't taking up living space and you need to have an engine fuel capacity to motor you long distances if you have no wind. You have to have enough water to take care of your needs between fill ups. Holding tank capacity is important if sailing in coastal waters, but obviously you can dump over board off shore. You have to have ice box/refrigeration capacity to keep your food cold for longer periods of time and a freezer is nice too. A genset is a great thing to have for longer distant cruising. As for electronics, a good chart plotter, VHF and even radar are handy things to have, but of course you can add them to any boat that doesn't have them. Sailing off shore, in the gulf stream, etc. can be difficult sometimes and so it is good to have a boat that can take tough conditions. That means, scuppers large enough to get rid of water quickly in the cockpit, bridge deck so water doesn't pour down in your cabin, good strong ports that can with stand smashing seas, windows that open for good cross ventilation, as well as hatches, nice deep bilges are nice for keeping water from sloshing around in your cabin sole. Bigger boats need windlasses for bringing in lots of heavy chain and big anchors to suit. Endeavors are built tough and are designed for offshore conditions. Catalinas are nice boats, but certainly not built as robust, aren't as heavily displaced, don't usually have large fuel or water tanks, don't have lots of places for storage and often are classified as coastal cruisers and not offshore (but various models may differ). Also, you have to think about the inboard and the horsepower to push the boat in extreme conditions. Many production boats have barely adequate inboards for coastal or inland use and some will offer engine upgrades for more bucks that really bring the HP up to what you really want for offshore use (and some mfg don't which means you are underpowered). So, please consider the things that matter.