What is the biggest aircraft that can be certified for single pilot operation? I know that the King Air 350 can be certified under provisions of FAR Part 23's Commuter category rules, which allow single-pilot operations in propeller-driven airplanes weighing more than 12,500 pounds and having fewer than 10 passenger seats. Order more than nine seats and the 350 must have two pilots at the helm. Does this mean you could certify somthing like an ATR 72 for single pilot operation provided it only had nine seats or less?! Surely there is an upper weight limit.
I specificly want to know about older aircraft such as the Howard 500 or a DC-3. I realise these are are very much hands on aircraft because of their age and you would be glad of a co-pilot to lighten the work load, but I would like to know could you A; physically fly somthing like a DC-3 on your own, B; could you do it legally, and C; would it require installing a lot of modern avionics?