My immediate thought was about this interesting sounding book [1]

http://www.amazon.com/Surreptitious-Software-Obfuscation-Wat...

Well, on attacking Virtual Machines, Rolf Rolles has the nicest work: http://static.usenix.org/event/woot09/tech/full_papers/rolle...

For building your own virtual machines, check out the ideas of the people here (Mips virtual machine should be easy, and enough to fool noobie-moderate level crackers) http://stackoverflow.com/questions/573115/what-is-your-favou...

For antidebugging tricks, Peter Ferrie has pretty much written the bible on these when it comes to Windows: http://pferrie.host22.com/papers/antidebug.pdf There's a couple of these papers, make sure you read all of them. For platforms other than Windows, you will have to come up with your own stuff, or Google well :)

For obfuscation, the best tricks are the ones you see in the real world. Check out the excellent Unpackme archives and tutorials of tuts4you: http://tuts4you.com/download.php

Another book on obfsucation that I see get mentioned a lot (which I don't recommend, but it still deserves a mention) is this one: http://www.amazon.com/Surreptitious-Software-Obfuscation-Wat...

And finally, if you're a noobie interested in getting involved in Reverse Engineering, check out Lena's excellent tutorial series: http://tuts4you.com/download.php?view.2876

If you want more info on anything specific, say so...