How do I get iTunes content for less?

It’s possible to spend hundreds of dollars on iTunes content, whether your poison is apps, music or movies. That’s fine if you’ve got the money to spend, but there are ways to lower your iTunes bills without smashing your iPhone into tiny pieces.
There are two key ways that you can save on your iTunes expenditure; one of them may well be obvious to you, while the other involves just a little bit more work.

Step One: NEVER pay full price for iTunes credit

iTunes cards are on sale, somewhere in Australia, roughly 75 per cent of the time.
OK, I admittedly plucked that figure out of thin air, but I’d be stunned if it wasn’t fundamentally accurate. One retailer or another is always having a “2x$20 cards for $30” or “Buy 2 get 1 free” or similar sale.

While retailer gift cards are usually just a credit lock-in — because you can’t cash them out and spend your money elsewhere — with discounted iTunes credit you’re at least getting a consideration in return for your money. If you’ve saved 20 per cent on the upfront cost of the card, then that 99c cent app is actually costing you 79.2c; that $2.19 song is only $1.75… and so on. I’ve never paid full price for an iTunes card, and I’ve spent quite a lot on apps over the past few years.

Step Two: Use International stores to your benefit.

I should point out that this is a technical breach of the terms and conditions of the Apple store, and as such it’s a loophole that Apple could close at any time. Equally, though, Apple’s position is that local song and movie prices are so high because of the record labels and movie studios, and you’re still paying for the content.
It’s also one of the best known “secrets” of iTunes buying out there, and it appears that Apple doesn’t really care that much about people running multiple iTunes accounts from different countries. Digital music and movies are where you’ll make the biggest savings here, as App pricing is fairly close — and if you’re buying discounted iTunes vouchers, probably cheaper in most cases.
The basics of this approach involve setting up a free account in the US iTunes store — or any other store where either the pricing or selection suits your tastes. You do this by trying to buy a “free” app (take your pick from just a few million of them; it doesn’t matter if you delete it straight away anyway), and then setting up accurate address details for the country of residence. Again, Apple doesn’t appear to care, given that it will, for example, accept 1 Infinite Loop, Cupertino as your new “home” address. Look it up if you don’t get why that should raise Apple’s ire.

You’ve then got to fund it with iTunes credit, which you’ll have to source online. I’m not going to pitch for any one seller over the other, as they vary, but be careful, because there are shonky operators out there. You’re also not going to be easily able to take advantage of iTunes price discounts, unless you happen to be travelling to the States and can buy cards in person.
How Do I? covers the basics, because we’ve all got to start somewhere.