Least Modern Bookstore In The Country

That would be Stacey's on Market. In all the time I've spent in San Francisco, not once did I go in there -- except, that is, until the other day, when I went it to see why it was failing.

Five things jumped out at me:

1. Underutilized space - too much of the floor space was underutilized - being either sparse or just not being maximized to see stuff and things
2. No cafe
3. An incredible view of Market from the 2nd floor, where a cafe should be - ideally, with a very long bar running across the length of the Market St window.
4. The 'STACEYS books' sign outside on Market is basically invisible. If you are a brand name, you can get away with using your name -- otherwise, just put a big 'BOOKS' sign up there. The 'books' on the sign is tiny and can barely be seen. No tourists would be interested to stop in, that's for sure.
5. The technical books they had seemed like a relic. I understand that old traditions die hard, but if it's killing your business, maybe you should think about ditching them? I noticed a few tech books in the back that absolutely nobody would be interested in.

In short, if I wanted a bookstore to fail, I would do exactly what Stacey's has done -- nothing.