I cannot imagine this being remotely worth WotC's time.
There are more things in Heaven and Earth, Dausuul, than are dreamt of in your imaginings.
For the print-on-demand option: Total nonstarter. Any such project will have a considerable start-up cost.
I'm not so sure that's true. Let's look at the steps you outlined in greater detail.
You've got to find a print-on-demand provider;
That's roughly the equivalent of calling lulu.com on the phone. Unless WotC has the worst long-distance provider EVAR, this won't register insofar as costs go.
In all seriousness, this is a bit more complicated, but not that much more.
Presuming it's a professional POD company, they'll likely have set rates, so that's nothing that need be worried about too much.
digitize anything you haven't already got in digital form;
This is the crux of it. Most of the actual time and effort will go into this step. That said, this would clearly be a secondary or even tertiary concern at WotC. We don't need them doing this fast or in bulk - at this point we'd be happy if they were doing it at all.
Also, I don't know what goes into having something put into digital form, but I'd presume that if you already have PDFs of something, it won't be that difficult or time-consuming.
get the files to said PoD provider;
Which is likely little more than sending some emails.
publicize the new offering;
I think you're overestimating this. Beyond the initial announcement of them releasing POD books, there's little need to advertise. And even if they were so inclined, it's little more than a posting on their website.
and maintain the relationship.
"Hey, did we get our check from the Lulu guys this month?"
"Yeah, it's right here."
"Oh good. Make sure it's deposited before the end of the day, okay?"
"Sure thing."
'nuff said.
All of this, so that you can put out books for $20+ (PoD is expensive) that anyone can get used on eBay for $10?
Here's a link to a 64-page d20 product at lulu.com for $15. And
here's a link to an eBay auction of the original 32-page S1 The Tomb of Horrors for $20.
In other words, it serves the consumer market just fine to have POD instead of eBay. That's not even considering how eBay doesn't always have what you want, you can get sniped in a bid or see the bidding get inflated (artificially or not), has no real guarantee of quality, etc.
Sell old issues of Dragon where any given issue has maybe 3-4 people interested in buying it?
That's a pretty major assumption on your part regarding how many people want older issues of
Dragon. The only major issue there is that some parts of the magazines - such as the comics - only had their first-publication rights purchased, but not the subsequent-printing rights. That's what got TSR into so much trouble with the
Dragon Magazine CD-ROM Archive.
Most likely, they'd have to sell copies of
Dragon without the pages containing that material, which'd be a bit of a shame.
In a world without eBay, it's conceivable you might be able to scrape a few pennies' profit. In this world--not a chance.
I don't think you're giving the world enough credit...or you're giving eBay too much.
For the .PDF option: Piracy issues aside, this might be able to turn a small profit. But Erik Mona posted in another thread about opportunity cost; it's highly applicable here. When you're deciding how your employees should spend their time, it's not enough for a given project simply to be profitable in an absolute sense. It has to be more profitable than all the other ways that employee could be spending his or her time. Otherwise you're leaving money on the table, and right now I don't think WotC has any to spare.
That's true, but a lot of what WotC's doing now doesn't seem to be as profitable as they'd like. I and a lot of others here are suggesting that this might be more profitable than you (and they at WotC) realize.
If you want stuff from old editions, that's why we have eBay and the like. Every so often I get a hankering to read one of the old books again, and I've never had trouble finding them.
You're lucky then, I've had trouble finding things I want on eBay plenty of times. And even more trouble finding the things I want on eBay for reasonable prices in good condition.