When bartering something of high worth for something of low worth, it is possible to garner more of the low worth items then are aloud by your dex, aka your current number of items limit.

Crullen.

Your version is logical but just seemed too obnoxious to us.

(Watch, someone else will post this in six months and it'll be changed, but that's my answer for now and I'm sticking to it.)

Clarification: Nothing obnoxious about your post, just the reality of having to clean out inventory to barter.