Here's the skinny, and I DO MEAN the skinny:
The model A block has a centerline spacing between bore 1&2, and 3&4 of 4.25". Stock bore is 3.875, leaving a theoretical web of 0.375 (3/8") between 1&2 amd 3&4 to compress and retain a gasket at pressures exceeding 10,000 psi. (25,000 psi with a HC head, hot cam, etc.). Subtract from that web width the chamfer put on top of the cylinders to permit the rings to get in during assembly. A very conservative chamfer is about 0.020", reducing that web 0.020 x 2 = 0.040". Most engine builders knock off a sloppy 0.030 to 0.045" when chamfering, leaving you with less. So, a stock web is at most 0.335", and possibly as little as .285". Add (subtract!!) to this the "tolerance" deviations from the non-obtainable perfectly machined block and you may have even less.
Now it's overbore time. At 0.080 over, you are down to a web of 0.255 to 0.205. The original gaskets no longer fit, the pistons hit the overhang. Gasket makers respond by reducing the web, making the gasket good to 0.125" overbore. An original Ford gasket, and an original Fel-Pro 7013 had a gasket web between Siamese cylinders of 5/16". The new 7013 R3, and gaskets from other manufacturers reduce the web to 3/16", a 40% loss!! Gasket blowout problems begin. On the positive side, most blocks still have sufficient "meat" to get by without sleeves.
Go for broke time (life beyond 0.125 over): At 0.156 over (4 1/32") you can fit stock pistons from Ford and other apps if you are prepared to deal with non-stock piston pin heights, requiring either longer rods or a crank with longer throws (stroked). SOME blocks, only those with cores that were dead on center during casting, and almost no rust scale loss in the jackets, will go 0.156 over, leaving a nail-biting 0.120 wall in places, measurable with an ultrasonic casting thickness meter. No self-respecting NASCAR $75,000 engine builder is without one! Diesel shops have this tool too. Everyone else, it's a crap shoot.
But wait! What about the web thickness that holds the gasket between siamese cylinders? At 0.156 over you are down to 0.179 (Less than 3/16") with a conservative chamfer, scrap iron or sleeve time if you take more. Every head gasket made will have some overhang, the pistons need a top chamfer to prevent striking the gasket, and NOBODY that goes 0.156 over is building a stocker with a conservative 10,000 psi at full throttle. They have a hot build up with way more cylinder pressure. Goodbye gasket?? Racers often went with solid copper (leaks everywhere!) or sealer and NO gasket (leaks everywhere!). They don't care, it just needs to run once, today, then we drain the water. Everyone else with a water tight multi-layer gasket on a street engine is living on borrowed time before blowout. Light foot? Maybe years. Hot motor, heavy foot? Maybe hours.
Does an overbore run hotter? At 0.156 over the cylinder wall surface area increases 4.8%, and with no other changes the displacement increase will be a bit less than 10%. The surface area is the major factor. Henry's 28-29 rad probably had a 25% over capacity when new, the 30-31 likely a 35% over capacity margin. Henry's truck rads were probably 50% over. If an overbore makes you run hot, your cooling system is crapped out, it's not the overbore to blame. Increased compression and better breathing cams decrease the waste heat into the block, they are not a problem either.