I'm more likely to pirate e-Books from authors I know and love even though I'd prefer to pay for them, because I can't be arsed to hack the DRM off on my own. Case in point is that Neal Stephenson's latest book, REAMDE (the plot is loosely about online games and virtual currency, in fact), I would gladly buy in hardcover at B&N for $19 since I would be able to pass that book around to my friends when I was done. If they weren't all 100 to 3000 miles away from me, that is. I'm rewarded by pirating the ebook instead because after reading it myself and verifying the quality of the book/DRM-free copy, I can just email it to my friends.
I'm more likely to pirate films and television series that I am most fond of, because it's more convenient for me to convert existing video files than to rip DVD/BD correctly on my own (and it takes up a lot of CPU time). If it's a series that is available on Netflix, I'll usually settle for that, but if it's something I really treasure, I'll want a higher definition video source to keep in my collection locally. The other day, I finally bought the Blu-Ray Matrix Boxset and The Fifth Element on Blu-Ray just because I knew it would be worth the trouble to have everything from these I want, ripped in maximum definition from my own legally-owned discs.
I'm more likely to BUY Steam-DRM PC games than pirate them because I have an appreciation for the community system that Steam created as well as achievements, and their support for some major free-to-play games.
I'm more likely to neither purchase nor pirate PC games that require a connection for their DRM. The only non-Subscription based, non-Steam game I've bought in the past several years (outside of the Humble deals) is The Sims 3 because I really was excited enough about the product to not care about what DRM was employed or whether or not I would be able to share the game or at least run it on multiple computers that belong to me under the same license (I can).
I'm more likely to BUY *SOME* DSI-Ware/VirtualConsole games because they aren't typically priced in the range of retail games so I can risk a few bucks on the chance a game I've never pirated or sampled winds up sucking (I got that new Air Hockey game from DSiWare for $2 and I hate it, but I didn't rage that I couldn't resell it to Gamestop or return my rights for partial store credit, which would be kind of cool but not in Nintendo's best interests to offer to customers yet). Some DSiWare/VirtualConsole games I would rather emulate/pirate, and since I can, I do.
As far as music goes I'll just be happy with Spotify & Youtube and continue to only purchase albums from artists I truly love and want to pay for enriching my life. I haven't actively pirated music for a VERY long time.