Astral, because ... you won't be making money. I'm tempted to say "ever", but I won't.
The reason is because there will always be farmers/grinders whose sole purpose is to get items and sell them, and because of the sheer man...well, not manpower, let's call it man-uselesseffort and time involved, will be getting a lot of items. Supply and demand will take care of the rest. Consequently, all but the rarest items will be flooding the market, and because there aren't, for now, any regulatory mechanisms in place to prevent such stuff, end up at a price so low it's not worth bothering.
Of course, if you DO get one of the (expected) amazingly rare items, you might succeed in selling it. But because there will always be people wasting their lives in front of the computers, now with the "NO MOM I MAKE REAL MONEY, SEE" mindset, there will always be items such as yours, for most likely lower price.
This is not taking initiative over the websites who sell Diablo 2 items. This is just legalizing them and their practices. They still get money, Blizz still doesn't, and technically never did lose money, because they didn't do anything worth the reimbursement. This is just a way to make their product generate revenue out of thin air for them from content that is already there. In a way it's even worse than the DLC craze that's been going on for quite some time, because they aren't even adding new items which people to buy. They're just letting people exchange money for time, and gaining a share of the money.
I can't say how objectively bad or good it will end up being, I can just say I personally despise it. But what I do (think I) know is that the average user is not likely to make a single dollar out of this.