Tiller vs. Wheel
Paisan, your theoretical 30 footer might weigh 4-5 tons while your theoretical 37 footer might weigh 9-10 tons. In addition, you could be sailing with a semi-balanced blade rudder, a partial skeg rudder (semi-balanced or not) or a barn door rudder with a full skeg. I don''t see how a general opinion about tiller or wheel (the latter offering greater mechanical advantage along with a host of other attributes and compromises) will help you when you begin narrowing down your search.
Better to approach it the other way around: first, which boat...and then, is there even a choice? (Usually there isn''t).