As Brian mentioned, low-friction sail track is great. The Dutchman works well, and I don't think full-time lazyjacks are anything bad -- they're good. If you get a full-battened main you don't need a Dutchman, as lazyjacks by themselves will help the sail fall in place nice enough. An electric winch can also be a big aid for raising the main. For a lot less money -- Some people are using 18v Milwaukee battery-operated right-angle drills and special bits that fit the winch-handle opening. http://www.thecranker.com/

As for mounting a windlass, it can be done on a cored deck but you will need a fiberglass pro (or some skill) to do the modifications and have it come out right. It's all about sealing and proper backing. You'll need an anchor locker directly below and a direct path over the bow roller. If you're not the do-it-yourself type you should definitely call a pro (or several) for advice on how to modify your boat. You'll want a foot control or remote handheld control at the bow, and another at the helm. You'll also need heavy-duty wiring and breaker to bring enough power to it and some installations add an extra battery in the bow for that load.

In the end, the total cost estimates of these mods will decide whether you should modify your own boat or trade-in. As for your question about power boat? Only you can answer that.