Wildman. A y-block will take serious over-boring of the cylinders without having to worry about reliability or overheating issues.
It's very common in some circles to bore a y-block 292 for '56 - '60 312 standard or standard oversize pistons. IF you take the 292 with its 3.75 inch bore and oversize it to the 312 bore of 3.800 you'll have 299 cubic inches using your 292 crank. IF you go to .040 oversize of the 312 bore, you'll be at 3.840 and have 306 cubic inches. The beauty of this is that you will be able to use over-the-counter available standard oversize pistons
Two cautions . . .
1) have your engine block sonic tested. Core shift in the casting process is common. IF there is core shift in your block, the machine shop may be able to slightly adjust the boring of an affected cylinder cylinder so that appropriate wall thickness is maintained.
2) have the complete rotating assembly of your engine balanced in doing your rebuild. Your engine will run smoother and your parts will last longer than they would otherwise. Individuals who do a lot of engine rebuilding will tell you that the original FoMoCo balancing was not-the-best back-in-the day.
Comments . . .
1) Sleeving cylinders is expensive. Sleeving 8 cylinders will seriously add up. I would recommend avoiding sleeving a y-block unless I didn't have other options. That said, we have one Forum member, Rowen, who has a 312 block that was totally sleeved for the purpose of reducing the cylinder bore to 292 size, IF I recall correctly.

2) I believe you'll find that you will have better fuel economy with your y-block than you would have with an FE engine in your truck.
Enjoy doing this project with your son!
NoShortcuts
a.k.a. Charlie Brown
near Syracuse, New York