you might consider splitting your live aboard and sailing interests. a combination of a liveaboard boat possibly with no motor and a small 18-24 sailboat to learn and explore on.
i suspect you would invest a lot less money and could learn more about what you really want- live aboard/seldom move or move under tow v. cruser. type of boat is also impacted by kind of sailing you want- daysailer, weekender, coastal crusier, or off shore. narrowing your criteria will help avoid some painful missteps