I have a very original 32 Tudor . I am also attracted to hotrods, especially Highboys. How hard is it to have a set up that goes form stock to highboy? Seems like my only issue is exhaust going from a header setup to a somewhat stock exhaust. I know a lot own one of each, but two tudors is WAY beyond my budget.
You have a beautiful car in great condition. Enjoy that with some modern upgrades in performance and brakes. If you want a highboy, simply take the fenders and running boards off. Those can be bolted back on any time and you kinda have two different cars. Use a different set of wheels when in highboy mode.
You can do as manyolcars said and just remove the fenders and running boards for the Highboy look but why not just buy a set of "hot rod" wheels and tires to swap over to the tudor when you want a hot rod look. Maybe 40 Ford Steelies with big and little tires on them and caps and rings for a hot rod look when you want it that can easily be be changed back to the stock wheels and tires in short order.
The first highboys were indeed created when guys took off the fenders, running boards, headlights etc to go racing then bolted everything back on at the end of the day. You could do the same now but it would get tiresome after you did it a couple times.