hmm vm's in the past.. pretty much all the major copy protections
most involve finding the handler (or handlers if there is more than one vm), of all, the safedisc one was probably the easiest, securom's one is tricky due to it varying a lot, starforce one is a bit harder due to it being ring 0 and ring 3 when i did it, and debugging it in ring 0 was annoying to say the least due to anti-softice, which then lead to me making my own driver to debug it
as for things being out of your league.. often it happens in reversing that people run before they can walk, like starting on hard protections without doing the easier ones first, which is a huge mistake, investing the time, seeing how the easier ones work then taking the ideas / methods u learned and using them on the hard ones definately has its benefits.. it all depends on your will and time, all i can recommend is plenty of note taking, making little tools etc.. and research (plenty of it)
often if you're lucky some games are released with different protections depending on the country of release, if you can obtain a copy of both, then crack them and compare them it can help immensely, or if you're lucker.. obtaining an unprotected exe..
you could also pick an older target, get the crack for it, attempt to make your own crack and reverse what the cracker did, and understand it.. many people learn that way