If you have a '58 block with no water cooling passages for the spark plugs, you have to either use the '58 only heads, or drill,tap,and plug the holes in the later heads. If you have a block with the water holes, you are OK to use the '59-65 heads. If you have a service replacement block with the provision for the hole,but no hole, it can be drilled OK. Use a 409 head gasket as a template to properly locate the hole. You can't use the '58 heads on a later block unless you plug the holes in the block. If you mismatch these parts, the result will be an exposed coolant passage that will pour water all over the place just beneath the spark plugs as you try to fill the radiator.Not a nice thing. The tri-power intake is an iron small port item, they never came on 409's new, I would grab an aluminum performance small port intake and a medium sized AFB and have at it. If the tri-power is your thing,remember that there are two sizes of Rochester 2 barrel. The '69-74 350 and 400 small blocks used a larger CFM carb, they are common and easy to find( unless you need a specific number)It would be possible to fab up three adapters and maybe make something work. 65 Pontiac tri-power set ups used a small center carb and large secondary carbs, the 66 on up set up used three large carbs. The optimal small port head was the 817 casting, found on 63-65 340 horse 409's. Not as pricey as 690 or 583 heads,either.I also heard that '58 blocks were rather thick,so rebuilding it wouldn't be a problem. Also, the non water passage '58 heads took a short spark plug like a 283 or 327. The long plug is for the 59-65 engines. If your heads have the long spark plug,and the piston doesn't destroy them, they're the later head with the cooling passage. I once was given a 348, upon disassembling it, somebody had put long plugs in a 58 head, the pistons were damaged, the electrodes were bent and broken, porcelain particles were in several cylinders, and the shells of the plugs were bent so the you couldn't remove them without cutting them off from the inside with a die grinder. Not a pretty scene.