I/we ran into this when fitting a small block Chevy head assembly onto a stovebolt six cylinder. The problem is the head bolt holes are anchored by the deck and the thick areas around the bores. So you would be limited more by the effects of loss of structure on the sealing ability because of the head attaching methods than the bore size. The reason I mention Darton is they specialize in exactly this. Their conversions remove the deck surface and head bolt holes and are sealed to the bottom of the bore and each other to prevent leaks. It is a very precise set of operations to fit the sleeves into the blocks. Lesser machines can't give the accuracy they demand. So it's not common sense, it's motivation and ability. If you really wanted to, and can afford it, I'm sure much larger bores could be used. But I'll bet money the cost of the engineering, the sleeves, and the installation work will be much more than a better block and that required machining would cost.