I pirate all my music. & films... and lots of US TV shows as the UK is ages behind & I do not have Sky TV.
Expensive & iPad software... I pirate too!

Aperture, CS5...
I'm pretty much scum!
I buy my iOS phone apps tho... and some cheap Mac OS apps, Divvy and Airlock etc....
I agree!
I buy so much music and DVDs that storing them is a pain so I have no issues downloading films too because I'll probably buy them eventually anyway. I'm into a lot of US shows that are either miles behind the UK or they've being snapped up by cable networks.
Supernatural - on ITV2 for 4 entire seasons, suddenly it's on a cable only channel, months after it's being on in the US and the first 4 seasons on DVD cost less than 3 months subscription anyway.
Smallville - After 9 years of Dawson's Crack style procrastination and female brow beating, I'd like to see Clark fly as soon as I possibly can at this point.
As far as software is concerned, I think some companies are complete rip off merchants and deserve the piracy because of the way they screw loyal customers just so they can keep using their software with more recent Mac OS X versions.
I bought a Pro Tools LE system based on a PCI card years ago, Avid only offered a cross grade to about £900 worth of Firewire interface so I did the only thing I could do when I moved up from Mac OS 9, spend £100s on the Mbox 2 Factory and get yet another licensed copy of Pro Tools LE, this time 7.4.
When Protools LE 8 came out, just over a year later (just my luck), it included all the plug-ins that made finding the factory bundle at a local music shop for barely more than the standard Mbox2 a wasted expense to start with.
To add insult to injury, they expected another £100 for a "licence" to download the upgrade when they've already left me with £100s worth of useless PCI card in a drawer and I don't even get a physical DVD with the software on.
I don't even accept the reasoning, "They're a business, they have to make money". They don't have to screw their customers, I'm not a company who can write it off as an expense, it's simply a hobby and and it's these unfair money grabbing tactics that give so called "pirates" a clear conscience.
I've already got 2 Pro Tools LE licences already and the hardware to prove it.
If the Mbox2 Micro had a combo headphone/optical output, I'd consider buying that at a later date so I at least have licensed copy of Pro Tools LE number 3 but it doesn't so I can't justify the expense when it's 1 quarter the cost of a used Mac Mini I could get more use out of.