I have a small roots blower weiand 144 on my monte. Holley says you can run it on a stock motor with stock boost (5 psi). Now what you have to consider is what goes with it.
1) The right carb (then time to tune it)
2) cowl hood 2" (unless you go with a centrifical blower a whole nother monster) Then paint
3) decent ign system (then time to tune again) not alot of timing esp in your case
4) fuel lines,throttle cable brackets, air cleaner, boost gauge (if wanted), fittings, all the small stuff
Now like others have said a stock motor with that many miles even a small supercharger will be the cause of death for sure. But if you want to have a good bit a fun for a short time...
I built my engine just for a supercharger, forged internals and good flowing heads. Not originally the supercharger of my choice but got a good deal. Its simple and produces gobs of torque even with stock pulleys.
Once again as others Im not recommending this for your engine but heres some info to chew on.