It's not just the amount of tailwheel time you have. The ability to easily fly different types of aircraft is not something that is taught in aviation - there is no endorsement or rating for it - yet oddly enough, it is a highly prized skill.aircraft like a Harvard, Stearman and Beech 18 are not fire breathing dragons to us. We have a decent amount of tailwheel time under our belts
The finest pilots - like Bob Hoover - display it, in spades. IIRC Bob Hoover set a record a few years back when he flew 60 different types of aircraft in one hour (!) at OSH.
These days, when somone "transitions" to a new type of aircraft, they are solemnly sent away for weeks of groundschool and simulator and flight training, and written and sim and flight tests, to learn from the gurus in some far-off land, about this mysterious new type of aircraft.
Most people only fly one or two types of aircraft. However, if you put the effort into flying as many different types of aircraft as you can, you will find it easier and easier to learn a new type of aircraft. After a while, you will be checking yourself out, because there's no one around that knows how to fly it. It might be a type of aircraft that has never flown before.
There are a couple skills you need to learn, to do this.
The first is systems knowledge. Not knowing about critical aircraft systems is stupid, and will kill you. You need to know, at a minimum, about the fuel system and the landing gear system. Embarrasing to do a forced landing on an empty tank, with fuel in another tank. Ask the comanche driver at Rockliffe about that. And, you probably want to know the gear speeds, which are never marked on the ASI or even placarded nearby, for some odd reason. It's nice to know about the emergency gear extension procedure, too. Pay attention to other systems that can really ruin your day. For example, on the L39, if I flick a couple of switches, I will have bleed air at 325C pumped into the cockpit. Not good.
The next skill is closed loop stick & rudder. Open loop flying doesn't deal with changing circumstances very well. You need to observe the results of your inputs and use that to modify your next inputs. Alex Henshaw, a crazy spitfire test pilot at the famous Castle Bromwich, flew fighters and bombers, puzzling everyone at the time, because "everyone knew" that a pilot could only fly fighters or bombers - but not both. But, Alex could. He was closed loop.
Fly as many different types as you can! It will make you a far better pilot.