Don't want to rain on your parade but I'd buy a trawler (twin screw) rather than a "broken" sailboat and trying to turn it into a trawler. You'll have more room, more tankage (Water, Fuel, and Waste), longer range, and as JohnB suggests, possbily more stability. Plus you'll avoid all the "What happened to your mast" comments. Good deals can be found on older trawler style boats and if it is for live aboard purposes, other than just the "Great Loop", see more room above. Don't stick yourself with something that no one else would want (for resale), unless you're getting it for close to nothing. I know someone will jump in my s**t (I don't really care) for being critical about your choice but use this as a continuation of your thought process. If you're thinking of the Great Loop I'm thinking of and you are from SD, you'll have to get the boat there by transport, which isn't really cheap from California. If the goal is the loop, you might want to shop in the Great Lakes area or somewhere in the east to save the transportation expense of getting there. OOps, sorry, I just checked and see that you indicated TN for your location. Good luck on your endeavor and don't forget, a bad day on a boat is better than a good day at work. Safe travels.
Dave