The pain-in-the-butt factor is purely personal preference, and if I have the record I don't see much reason to digitize it as I would rather listen to the record when I'm home. I have over 2,000 CDs ripped so that is plenty of portable music if I want, not that I do that very much. I have made a few copies of OOP records on CD for friends, and I have some old cassettes of OOP stuff that I've digitized so that is nice, but for me, and that is the key, for me it is generally a pain to do. I've got maybe 3,000 LPs and I'm not going to live long enough to digitize them :>(
As for the spdif comment; the pro converters I mentioned above have USB and/or firewire outputs if that is a concern.
The fidelity from VHS tapes is clearly inferior. Check the specs. If just being analog is the criteria then 8-track is analog too.