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I am installing my baseboards, and there is a section that must be attached to brick. I know, by experience, that the best nail for my type of brick is the hard-cut masonry nail (and not the fluted nail).
What is the best way to drive the hard-cut nail into the wooden baseboards to prevent splitting? Should the wider surface of the nail be driven perpendicular or parallel to the grain? Should I pre-drill the wood?
Parallel to the grain with a pilot as mentioned by wallyk. The pilot hole can be slightly larger than the tip of the nail since the whole nail is tapered. Choose your length of nail to be long enough to go 1" into the mortar joint. Some brick will take a nail, depending on how old they are. I have driven regular common nails in older brick and brick joints. You can even set the cut nail with another cut nail but not by driving it the same way you did the nail that is doing the holding. Since the nail is flat, hold the nail by the smaller end, and the broad head is used to set the other nail by placing the narrow edge of the head to the nail to be set. The hammer strike has to be clean and solid, if not the nail that is being used to set the other nail will spin rapidly as the nail rotates to the flat side and make your fingers sting. I tried to locate an illustration to help show, but one did not come up on the search I gave. You could use a regular nail set but it will be tricky.
Definitely pre-drill the wood. By removing the material, the nail doesn't have an opportunity to wedge open a crack.
To make it trouble-free long-term, make the drilled hole just a little smaller than the nail shaft for a tight fit.
Use construction adhesive or pre-drill trim (with countersink) and brick and use masonry screws (tapcon) or anchors. Else be prepared to learn new 4-letter words if you decide to use nails.
