Coming from an all-analog-all-the-time world, I'm less sure analog sounds better. Good analog gear sounds great, but then so does great digital.
As far as ITB goes, recall matters to me, as do quick turnarounds, so I love it when I can work entirely ITB! Since coming to Sound Images, where ironically I have more OTB options than ever, I've managed to get most jobs done essentially "ITB" and have never felt I was sacrificing sound quality in any way.
The caveat here: I use MH +DSP hardware with some very "special" tools, and "roll my own" plugs for stuff I can't buy, running in soundBlade. I have a PT/TDM rig that I use daily for sound design, VO and commercial production, but TDM itself, even in HD, is more of an obstacle to great digital than an enabler, so it's rarely if ever used for mastering. If I were mastering in PT, I don't think I would be as confident about ITB sound quality, since it's becoming such a standard on the production side, it's worth noting in this conversation.
-d-