Without getting into the math , have you considered that you will have to have a blow through carburetor, and oil supply, and return. Then there is the aspect of retarding the ignition as boost levels increase, as well as fuel rate. Also there is the question of if the intake manifold would stay sealed under pressure. As far as size wise, what you would have to figure is how many cfm your turbo puts out at whatever psi you are shooting for versus the volumetric efficiency of the engine , and cubic inches at whatever rpm that you want to be your butter zone, keeping in mind that number needs to come in before you get on top of the cam. You may find that the boost comes in a lot later than your useable RPM, especially if its in a work truck. I m going to assume, because I don t know, that 292 is probably an 8 to 1 compression ratio, so its low enough for boost to make a big difference. What I don t know is where the cylinder head and or bolts quit sealing at say X amount of pressure. I also don t know at what point that the rods will make a windar in the block. 302 Jimmys have had great success in years past under boost, but at the time the aftermarket supported them.
As far as feeling stupid, I gained the knowledge that I have from tearing stuff up. The difference is, what I was tearing up was readily available if the magic smoke was let out of it. I m all for you experimenting. Buy a little welder and some tubing, and go to town. What I would recommend doing though is playing around with easily replaceable modern engines. This also becomes important regarding ring seal. I had a 502 that I had named "dipstick". Even with open element breathers it would blow the dipstick out at around 18 psi of boost.
If you pursue this in a carbureted application, I very much recommend installing a fuel ratio gauge so you don t lean burn. Run a bit fatter than stoichiometric ratio, and let your plugs tell you the tale.