I doubt it. I would believe that the id guys weren't too choked about the lost revenue after the fact, but the business guys probably believed the scheme would work (especially since they contracted a company that said "yes, this will work").
Aside from that, the shareware cd was incredible marketing - the digipak cd case was the kind of art and paper construction that nin was using on their discs (like the Broken EP), and the disc itself has nice art with the four logos in cardinal directions. I bought a copy of the registered disc from ebay years later and it's in a jewel case with really crappy artwork vs the shareware version, it was a surprising disappointment.
That was pretty tough in that day and age. Especially from pirate sites.
mIRC had some good servers but getting someone to keep a direct connection with you for that long was problematic too.
And then if you didn't have a dedicated phone line for the modem...
Although you still wouldn't download a CD, simply because... you wouldn't have been able to take it home with you! Hard drives were in many cases smaller than a single CD. Anything more than a few 10s of MBs would have been considered excessive.
well, if dialup cost more than just buying the game, it makes sense to buy it rather than pirate. also, if you care about audio then you'll get the cd, becuse downloading 400MB of audio over dialup isn't fun.
compared to that a crack is just a single binary.
But in any case physical copy + crack was the best solution at the time.