Around 45~50 years ago I had one (think it was 1957 engine) that leaked just like that. Removed head, discovered the block surface should have been resurfaced but couldn't do that at the time. So I cleaned it up as best as I could and reassembled with new head gasket. Used a new (back then) spray-on gasket sealer which was supposed to be the best product for things like this. After that the leak was reduced greatly but you'd still see a bit at times. The good news is it never went into the cylinders nor the oil pan. I've never heard of the bolt hole problem, however maybe others have. If the bolts were bottoming out before they got tight enough, this sort of problem might happen, but you could check that pretty easily with a ruler, I'd think.
