Quoted: I beleive that the most common place that these engines leak is at the rear intake manifold where it meats the block and heads. People replace the gaskets and forget to put a big glob of RTV in the corners.
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I have built several small blocks and have been around the street rod world for quite a while. That valley gasket should be the first thing trashed out of the gasket set. All I use is a bead of black RTV (silicone) sealant and it never leaks. Another common leak is around the bolts from the intake to the head. If the threads aren't sealed well, it will leak at the center bolts.
Rear seals can be a problem, but if you install split seals with a small dab of silicone at the split and then set them offset to the main cap split, along with placing a very tiny amount at the rear main split on the iron, it won't leak. Also it must be installed in the correct direction and pre-lubed to prevent start-up burn.
The later model rear main seal appliance that is a one piece seal can also fail if it isn't pre-lubed. This happened in less than 10K miles with a factory assembled motor (to me).
There is also a through-hole on the front of older blocks that allows you to install a long bolt to hold the fuel pump pushrod in place while installing the fuel pump. Folks commonly forget to plug this bolt hole and oil will leak when you brake hard, particularly if you are a half quart high on oil.
Yes they can leak. No they don't leak, if they are built correctly.