If I'm playing this game I'm finding a 273 block and I'm finding old heads with different size valves and I'm setting them up with checking springs and pushing the valves down into the bore until they hit the cylinder walls. You can't measure the valves in the head from outside to outside and say, "Oh that is smaller than the bore, I'm okay." The valve does not open parallel to the bore but at an angle and as it opens it gets closer to the cylinder walls as the wall curves in around the bore.
The more you mill the heads to get compression, the more you lower the valve into the bore and the greater interference you get. Bigger valves, greater lift, milled heads, smaller bore, zero deck and pretty soon you are notching the bore down into where the top ring seals.
I'm just sayin', this is gonna be expensive when you stretch the limits. Take the time to check carefully.