Crossing that line
Once you get above 25 feet, you have crossed that magic line: sailboats longer than that are generally not made to be "trailerable". You can put some 27 footers on a trailer, heck, you can put any boat on a trailer, but they are not designed to be trailered (like the Oday 25 was). A 27 foot boat is not just two feet longer, its also much heavier and has more volume. If you want a centerboard boat because of its shoal draft capabilities, then there are some options for you in the 27-30 foot range, but these are not true trailerable boats. If you really want to be able to take your boat to distant locations on even a semi-regular basis, you already have about the biggest, heaviest trailerable boat made.