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Yes sir, you will have to remove the dowel pins in the older block, but it will all bolt right up. Got a buddy that had a good older 350, and blew up his vortec. Threw his vortec heads on it, reluctor wheel, crank sensor, accessories, and drilled a hole for the knock sensor. It all fit like a glove.
No, the cam and lifters and spider will not work. The lifter bores are too shallow in the older block, and there is nothing to bolt the spider to. If you wish to go roller, you need an aftermarket roller kit designed for your application. You have to match your timing set to your cam, the roller cam timing gear will not bolt to a flat tappet cam.
rollers on a flat tappet, no. I would not suggest going mechanical, it will require adjustments every few thousand miles. You will need the correct length pushrods. I forget which ones you need.