Una, great questions!
It wasn't hard for me to do this -- for one week. I predict it will get harder in the sense that I will be repeating outfits in some silhouettes really quickly. But since I like to repeat outfits, I also predict that won't bother me. In other words, long term, maybe I'll discover that I can keep a leaner wardrobe as an "outfit" shopper rather than as a "separates" shopper. If I choose to do that. (Which I'm not sure I will).
For me, the no-brainers are the FFB outfits of skinnies plus pullovers. The lightbulb moment came a bit earlier with the purchase of a casual dress. Adding a dress really increased my possible work-at-home options. Even one dress. Because I can "accesorize" it (or disguise it, if you prefer) with different pullovers, cardigans, scarves, and tights. Ha!
kkards -- I am not sure yet whether I will need glasses any more. The hope is that I'll be spec-free, but I rather expect that I'll need drugstore reading glasses for certain reading tasks or low light situations. My distance vision should be good. It's possible my eyes won't adapt to the intermediate zone all that well, either -- only time will tell. I'll need about a month before I know for sure. But since I needed correction at all levels before, and quite high correction, any freedom from specs will be a huge boon to me, even if it is partial.