As a roofer I would never recommend nailing a board to the roof in such a manner, however, painters/siders/stucco guys do it to new roofs all the time, as long as you fill the leftover holes with tar(blackjack at totem sells for a couple bucks a tube) you shouldn't really have any problems if it's a one off thing. If you're doing this every year though your shingles are gonna become a mess awfully fast and that might lead to problems down the road.
Looking at your roof because you have interlocking shingles what you can do is carefully "unlock" a couple of the shingles and lift up the shingle and nail your 2x4 under there. Then once you're done you can remove the 2x4 and carefully relock the shingles and the nail holes from the 2x4 will never be exposed. If you have a older roof or it is really cold it can be very easy to rip the shingles though so you need to be careful.
If you need a bit better directions let me know and i can try to get some pictures of the process step by step,
Last edited by Dan02; 11-15-2008 at 12:49 AM.
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