So I am not paying over the odds if I buy from a bricks and mortar store. In fact I am saving money, since I don't need to burn a downloaded copy onto CD or DVD, print a label for it, and buy a jewel case for it. None of those items cost a great deal, but the time putting them together does. If I factor in the cost of printer ink to do a fancy colour label, then the cost does become significant.
Looking at my copies of iWork '08 and OS X Tiger, there was no wasted packaging (ignoring shrink wrap). I don't need to print out the Introductory Guide for iWork either.
Plus I believe I can sell a physical retail copy of Apple software* on Ricardo if I no longer need it.
* The licensing conditions do not allow you to sell the copy of OS X which came with your system, but you can sell a copy of OS X which you bought as a standalone retail product.
As for no wasted packaging: when the product is available with no packaging at all, then all other packaging is a waste, shrink wrap or not.
Regarding selling it on, I have no idea about the legality of that, but again, why bother when you don't have to? It's a lot easier just to delete a file.
All of this just seems like a lot of unnecessary hassle to me, but as I say each to their own. My father still wastes entire forests by printing out reams of web pages which he finds interesting, despite my protestations.
If you are faced with a system disk failure and have to rebuild it, it's far faster to reinstall from CD / DVD than navigate through* all the sites you have downloaded software from and re-download. You cannot guarantee that the software will always be downloadable. Some sites may disappear altogether, others may introduce a charge for what was previously free. Other products may simply be withdrawn. If a future version of the software has minimum requirements which exceed those of the current product, you might not be able to use it. You might simply not like a future version of the software. If I pay for a software product, I want to protect my investment. See 2, 3, 4.
There's also the problem of software keys for products purchased online. I would recommend stashing the key on the same backup CD / DVD as the software product.
* A lot of freeware stuff shifts location over time. It can be time consuming to find its new location.
As always I guess it boils down to what you use your computer(s) for. As someone who uses my kit to mostly capture, store and playback multimedia (of which the only essentials are some photos), there is no way I would waste time or expense messing around with CD / DVDs for this kind of purpose. Backing up family photos - sure, but that's another thing altogether. Everything else is just backed up to a Drobo. Not failsafe by any means, but good enough to make the risk calculation work for me.
However, I'm sure there are other scenarios / uses where what you describe makes perfect sense, so thanks for the food for thought.
(Going back to the original point, I still wouldn't bother buying iWork 09 over the counter though....
Sorry, couldn't resist )