I think this is pretty much right. For excellent shows I love to pay up front to have it right away, but if I know that within a year a replacement set is coming for cheaper that makes me think twice about the considerable amount of "good" shows. I only have so much money to throw around. I have wondered why no one seemingly ever cuts the MSRP price instead of paying for new packaging.
I think the oddest example of this marketing lately is Tsubasa. They box up season two in late Deceraber, then release a complete collection of the entire thing three weeks later. Now I can understand releasing season two for all the people that purchased the season one box, but to make the season releases obsolete that quickly?
Another big offender: rebuild of Evangelion. Everyone paying attention knows that 1.11 is the superior release, but we still got a release of 1.01 that is only relevant for four months.
Mind you, none of this is necessarily as egregious as Bandai stretching the second halves of Gundam 00 and Code Geass to four volumes instead of three, be this out of perceived necessity or not. Nor is it nearly as bad as rab being married to single volumes even now, and for C-list "skeezy" titles no less (seriously--$90 MSRP for 13 episodes?! Anyone who falls for this deserves to be ripped off). But still.
I think redundant stocking may be steadily becoming a thing of the past. At my Best Buy almost everything is current except for Haruhi Suzumiya (they have the box and a handful of the original LE box). Fate/Stay Night had two different boxes but the original has since disappeared, and in fact you can't even buy the original box at a normal retailer now. They all say it's been discontinued. I think there's been a bit of a shift perhaps from even a year ago, where I could easily find drastically different versions of Samurai 7 and no small nuraber of singles standing alongside infinitely cheaper boxes. Heck, relatively cheap Bandai stuff occupies significant shelf space now, whereas at one point we had a thread about how their stuff was nearly absent from B&M stores.
One interesting angle to this is Blu-Ray. High-def is only growing, and if memory serves it's been said at various industry panels at roughly half of Funi's market (at the very least) have what they need for HD media. For older shows, the release rights seem to come however quickly they can be acquired. Not only that, but the Blu-Ray versions for Funi's recent complete series releases somehow end up costing exactly the same as the DVD version--something I find as astonishing as it is impressive. So for some fans the question may have become not only "should I wait for this to get cheaper?" but also "should I wait for Blu-Ray, especially since I know it won't destroy my wallet?".
Fortunately, this is an issue that will probably diminish as time goes on. At the very least films like Evangelion 1.11 and Sword of the Stranger get released simultaneously, and if the early reports are true we'll have Fullmetal Alchemist: Brotherhood getting newly released on DVD and Blu-Ray at the same time. Of course, at the same time, we have a fan favorite like Soul Eater on DVD only for the time being.