Brainstorming an Idea, whats your 2 cents

I would not mill those pistons, there are sets specifically designed for stroker applications which wont require any machining.

I dont think the flywheel from a truck motor is the same size, I believe they are larger, at least in the old days they were. If your motor is externally balanced the flywheel wont work with the stroker crank anyway. It would need rebalancing to match the crank rod pistons etc.

I'd take the motor as is and put in a healthier cam matched for your intended application - car, axle ratio, trans type, etc., and use it.

Meanwhile I'd collect a good core block and the pieces to build a stroker from scratch, once done, sell the 360 as a running piece. All you'd be loosing is the cost of machining the block for the new motor, because you'd want to go thru the old motor anyway.. at least I would. You might actually come out better money wise selling the other engine as a whole running piece, depending on what you get for it.

My .02....good luck deciding !