..Except that Aniplex has used this model in the US, and for most of their BDs/DVDs, they've sold very well for their price point.
I remember that I thought the same way you did when Aniplex first started to branch out to the US with Kara no Kyoukai (Garden of the Sinners). I went to their premier at New People in Japantown, SF and laughed when they told the audience that we could own all 7 movies in the deluxe box for $500. A quick Google search shows that it's out of stock on Rightstuf at a price of $319.98 for the standard edition. That tells me that there are at least some folks out there that don't mind coughing up $300+ for physical releases. I also seem to recall that Aniplex did the same with Madoka Magica, and the limited edition Blu-Ray box sets have only increased in price since their initial release.
Funi is doing is what Aniplex is doing. Funi believes that Cowboy Bebop is a hot enough property for people to want to still shell out hundreds of dollars on a new release. Assuming this is a US version only exclusive, they've spent some serious cash designing these new books, packaging and limited edition tchotchkes. Unlike most of Aniplex's US releases, CB has been released multiple times in the past. The tchotchkes might be the only thing enticing fans to consider buying the series again, particularly at the prices Funi wants. So, it'll be interesting to see if US fans, despite having access to the series and perhaps already owning multiple versions of its release, want to spend $500 to buy the series again. My guess is that this particular release will be Funi's experiment to see what their clientele is willing to spend and what sort of premium items, if any, they value most. If the Bebop fans are wise, they'll see the writing on the wall and not want to send that sort of message to Funi.