Cody, as I think you know, the longer the stroke, the more cylinder side wall loading will occur. It's a natrual thing. The 383 is a good block to start with and HP limits are high enuff to be able to turn the engine into a super great machine. OF course, heavy right foots shorten the best built engines life down alot. All the insides should be forged. So power handling shouldn't be a problem.
The 383 is a short stroke engine that will like to rev. IF you stay at this CID, you'll just have to be careful of over camming the engine since a short stroke engine is weak in torque. To build up torque in any engine, you'll have to eye ball the total package and the little things that go with it. It's just a nice thing that the engines natural CID is (for the time it was built) generaly large.
Also, remember that the engine is old, so alot of things your modern car has, your taking for granted without really realizing you have. Computers really add to the car alot these days. While I'm not suggesting to add one, the rest of the engine is very close to basic as it gets.
Use things like a good use of a quenched area on higher comp. pistons. (Not for super charging) Zero gap rings, possibilty of coatings on the piston crowns and in the head chambers after a polishing, use of a roller cam over a Hyd. which will hand out not only HP, but torque and lots of it, roller rockers etc.........
One of the interesting and cool things about a old car, any old car, is that the engine is a basic slate of what possiblitiy's are out there and what can be done to it. I love the fuel injection idea. It will add so much driveability to the car and ease of operation for Dad.
On super chargers, while they can shorten an engines life, it's also made with a direct connection with the right foots weight and it's life span. A 6-71 / 8-71 roots style super charger make crazy torque on demand from idle to redline. A Hair dryer (Vortex, paxton) style unit comes on softer and builds up for a softer addition of pressurized power and isn't so brutal on the crank and other internal parts.
Theres alot of stroker options out there to choose from.