Recently, I was asked where the best place to find a good deal on Microsoft's Windows 7 operating system would be. Having used the RC, I knew I would be upgrading so I preordered up a couple of the $50 Home Premium copies that lasted for only two weeks back in June/July 2009 (in hindsight, I wish I would have picked up a few more copies for friends & family). Since then I haven't needed to purchase individual licenses and this put me into the position of not really knowing what deals exist right now for the average person other than the assumption there were non-profit, educational, OEM, MSDN member, etc. pricing. I also knew the family pack deal was dead.
[Update 2010-09-02: The family pack is making a comeback as of October 22, 2010; no word on how long the promotion will last yet]
In the end, we saw that there are still a few inexpensive (and legal) upgrade options found in the top search results and also through our own research. Note that I am excluding the Windows Anytime Upgrades since those are for adding features to an already purchased copy of Windows 7 and also OEM pricing since that's for system builders only. Read further for our findings.
First of all, if you are currently enrolled as a student in a college or university with at least half a credit, go right now to the Microsoft Student page for Windows 7 and qualify yourself for a hugely discounted price ($30 for Win 7 Home Premium Upgrade or $65 for Professional). You'll also find good prices on other applications such as Microsoft Office (Office Ultimate is $60). The promotion is called by Microsoft "The Ultimate Steal" and is good through December 31, 2010.
Edit: It looks like Home Premium may no longer be available, just Professional
Just by shopping around on the Web (Amazon.com, Buy.com, Walmart.com, BestBuy.com, Newegg.com, etc.), sometimes you can find nice deals. Unfortunately, with Windows 7, pricing is fairly consistent across resellers, though it looks like buying directly from Microsoft is not a good option due to them charging full retail price just for the downloadable version and then charging you another $15 for the physical CD! From our searching, the best upgrade price found for Windows 7 Home Premium was at Amazon.com and Walmart.com for $102.54, but Amazon wins out by $3 for including free shipping. For Windows 7 Ultimate it's the same two contenders at a price of $193.54. For Windows 7 Professional, Amazon wins at $172.00 with Wal-mart close behind at $174.54 plus shipping. So, if you're looking to trim $20+ bucks off your purchase price, it's worth looking around.
Parents, Students, School Teachers\Faculty\Staff, & Non-Profit Organizations (NPO)
If you are a parent of a child that attends a K12 school, college level university or even if you home school your children, you can often get a really reduced price on software for your home computer, assuming your child will be using the family computer for school work. Teachers, faculty and staff of an educational or non-profit organization may also qualify for discounts.
A good example of this would be the Academic Superstore. If you check out their Windows 7 page, you will see some very good upgrade prices for the downloadable versions of Windows 7 Professional ($79.98) and Ultimate ($99.98) versions, as long as you can provide a valid eligibility document. The discounted physical (i.e., non-download version) product pricing requires you to be associated with a qualifying school.
Since deals and promotions come and go, finding the best one can be hard at times and the winners tend to change by the minute. Even so, the prices we found look to be fairly solid for the time being and are a good starting point for your own quest for Windows 7 on the cheap or if you need to point a friend or family member in the right direction. If you come across any other really good deals or alternatives, post them in the comments or shoot us a note!