Reactive rigs

For the last couple of years I've been sailing on a type of boat that might by todays standards be classified as a sportboat, (Wylie Wabbit) it's 24 feet and 5' 7'' wide, weighs about 975 pounds empty. The rig is pretty old fashioned, going upwind I have to work the backstay constantly to maintain proper balance, ( there is no traveller) so my question is, what size boat is the maximum for an effective reactive (skiff type) rig? And, what are the issues as the size of boat increases?

Love to hear your input,
Yokebutt.

 

Bethwaite has launched a 26' sportsboat (79er), look up the Bethwaite design website for pics and that may tell you something.