Live aboard a Helms 25?
Are you going to single hand or one other crew person aboard? If so I would stay under 36 ft. Much bigger than that and they are hard to sail shorthanded. Not to say that it can''t be done, but more work. Who wants to work.
Also keep in mind the bigger the boat the more bucks to do the upkeep. If a bottom job on a 30 foot boat cost 800 dollars a 36 foot boat would be about 2,000 bucks. There is more of everything and and everything id bigger.
I sail therefore I ARRRRRRRrrrrrgh