The only place you can get a discount on Apple-branded software is from the Apple Store or your college or university bookstore. The discounts for smaller items like iLife and iWork aren't very substantial (like $9US), but the price of something like Final Cut Studio is $600 cheaper in Apple's education store than the regular store.
Although the academic software market has become more equalized in terms of pricing, it still pays to shop around, as some stores have better discounts or bundles than others. Before buying from any online store offering academic discounts, make sure they are certified to sell the software they are selling.
I have ordered the majority of my software from Academic Superstore and JourneyEd and have had great success at both places. JourneyEd also has a European portal.
It pays to compare software, even for titles that are already academically priced; Microsoft Office 2008 Student & Teacher edition, already discounted for academia, is $10 less from Academic Superstore or JourneyEd than it is at the Apple Store.
Check with the software publisher
Although online software stores will usually still offer the best price, it pays to check with the software publisher to see if they either have their own academic discount or a special promotion. For instance, Microsoft has an entire page dedicated to its academic pricing. Some schools or institutions have special arrangements with Microsoft to provide even lower prices or better bundles. Adobe's Education Store doesn't offer lower prices than the education outlets, but they might offer a version or a specific product that the academic stores do not.
Check with your school
Although my university's bookstore was completely overpriced, some colleges or universities offer better discounts inside the store than you can find online. Also check with your school's technology department to see if there are additional discounts available. Although my school's bookstore sold Windows XP for nearly the retail price, the technology department offered licenses for $10. Also check within your school of study to see if there are other discounts or special available. I was able to get a better price on some Avid software because the College of Arts & Sciences had a pre-existing relationship with the vendor.
Have your verification data ready
To buy academic software, you have to prove that you are an eligible student or faculty member. Usually, this just requires faxing or e-mailing a copy of a student or faculty ID and a class schedule for the upcoming semester, or some other document that shows you are enrolled in school. JourneyEd and some other academic retailers are actively collaborating with colleges and universities so that you can verify your enrollment digitally, without having to fax or e-mail anything, but make sure you read the requirements and have the necessary information ready.
This is a tip for anyone who needs a Windows license to use with Parallels or VMWare Fusion: buy an OEM license. The academic prices for Windows XP and Windows Vista are for upgrades only. Unfortunately, getting that to work for a virtual machine installation is more headache and trouble than it is worth. The prices, even with an academic discount, for the full version of either OS are ridiculous. You can save an enormous amount of money by purchasing the OEM System Builders license of Vista or XP. Pair that with a $40 academic copy of VMWare Fusion and you can have a full Windows setup on your Mac for under $150.
Don't forget indie developers
Although the bigger software companies (Adobe, Microsoft, Avid, Corel) offer the easiest to find discounts, a number of independent Mac developers offer educational discounts as well. TextMate offers an academic discount (I believe it is 10%) and other developers do too, so it pays to check the store for academic options.
Do you have any other tips for saving money on academic software? Leave your thoughts in the comments!