Deborah, those are great questions! Thank you.
1. It is totally comfortable. The zipper is actually two way, so if I am sitting I can open it from the bottom. (Can also do this for a slightly different look -- but it wouldn't offer genuine warmth worn that way, of course.) The wool is very, very soft and so is the leather. No prickliness.
2. I can't know for sure if I will be happy with the grey. It suits me and looks nice, but it might pall during our very grey season. And any hat I choose would have to be super simple. So this is truly an unknown. OTOH, I haven't tired of my grey sweaters.
3. Since my colour palette is basically blue, grey, some winter white, and a bit of berry and plum, and since I tend to wear denim in various cuts, almond or pointy toed booties or boots, and semi-tucked pullovers for my regular wear, I think this will play easily with my clothes. It won't work very well (if at all) with skirts and dresses. But I have few of those for winter. It does not layer all that well over a jacket. So that limits the type of outfits it can be worn with, for sure. Basically, we are talking about a city walking coat for pants -wearing days. However, since that describes the majority of my life, I think it's fair to say I will get enough wear from it.
4. I have a couple of other bags that might work -- a big reptile embossed charcoal tote; my black and cream colour blocked tote; a dark red crossbody. My bag selection is very small anyway. I am not worried if I decide I need another bag to wear with this -- I have been hoping to get a few more bags this winter anyway, but simply haven't seen the right ones.
5. Yes. It works with my moto boots (shown), pointy toed ink booties (shown), almond toed black booties, black knee highs, grey heeled knee highs, and grey mid-calf snow boots. Could also work with my cranberry booties, although I doubt I would wear those with it terribly often. Will also work nicely with my SE Petty snakeskin booties.
All in all, I think it's a good and dramatic addition to the wardrobe and I plan to keep. Thank you all for your thoughts!! And now, please stop me also lusting after the one that Dianthus posted!