1) It´s doable and it´s no mamuth sink of money and manpower if done with competent people. Granted, it´s still time-consuming.
Time is money. Competent people are money. If it consumes time, they need to pay someone for that time.
As a business, when you are going to spend time, money, or resources on a project, you must ask not only whether the project will make you money, but will it make more money than the other things you could spend those resources on.
I have $10,000 to spend on a project. Do I spend it on the project that will return $1000 over my investment, or the thing that will return $5000 over the investment? No brainer, right? SO, why on earth do we think that this work on old stuff will net them more than work on new stuff?
Most of it already IS digitized.
My understanding was that some of the books had been scanned, and the images put into PDFs. That's not yet digitized in the sense that the text itself can be manipulated. There'd still be massive OCR and editing steps.
If the VTT does integrate rules into it to bring up displays ons creen of monsters or such, and this can also be used to pull data form the older edition compendiums... in a <blank>ing heartbeat!
Well, that's still more work. Character builders, monster builders, treasure builders, all more work.
Lots and lots of work - everyone asks why they don't do it, and when you look at the list of work needed, it isn't short - and how many people *outside* of the squeaky wheels on message boards are playing these games?
I don't fathom them ever making tools as decent a there was for AD&D, and those were even lacking in functionality.
I don't know what tools you are talking about. WotC stopped supporting AD&D (1e) back in 1989. That's before WIndows 95 and Internet Explorer. I don't believe they had any computer tools of consequence back in the day.