I completely agree about the added analogue generation making no difference to my ears but I suppose one has to be fair to the DATheads of yesteryear: when people were trading DATs, I guess it would be possible for a recording to undergo many non-digital transfers, which might have a cumlative effect on the sound.
Nowadays, with most sharing and trading being done via FLACs, the effects of that initial analogue transfer are probably negligable.
That said, if I could get a clean digital transfer of my tapes, that would be the way I would go.