I don't know the American models but its safe to buy on good condition and always consider resale for when you want to change either up or down.
Length equals boat speed which is handy, helping keep trip times down.
Performance yacht are worth including in your list as a good platform for learning, the better pointing ability of performance yachts is also handy. You can always reef a performance yacht without much compromise whereas slower yachts need all that keel because they have trouble avoiding bad weather.
Consider joining a club to take advantage of the help others will offer.