This is such a neat situation to be in. I can understand your mindset in wanting to do a little modernization/upgrading while things are in a state where it is easier now than it will be later. Allow me a few lines here for a few thoughts. Befriend someone with a similarly built Hot Rod that is driving and stopping. I am talking early OHV V8, Early hydraulic drum brakes and period but dialed in steering. Maybe that person will let you drive it. You may be quite surprised how well that old "junk" works on a light weight Hot Rod. Now if you "Must" upgrade. Maybe just a good rebuild on the 283 with hotter cam, some work on the heads and a dual quad intake. With running the fenders, hiding a modern overdrive transmission may be a stealth option (think 700r4). If you want disc brakes, there are covers to hide them and keep the drum look. Need to strengthen the frame? Perhaps an old stock later 30s "X" section is just the ticket. Maybe a new pair of springs and oil (not gas ) shocks will get the ride where you want it. VW restoration Empi brand shocks are cheap and may be "It". That said I would strive to ride in or drive a similar one before scripting big changes right off the bat. Hit up a couple Traditional focused car shows too. This place is contagious for its enthusiasm for keeping these things old school. It looks like that is taking effect on you. Have fun with this regardless of what direction you go with it.