Excellent summary. Regarding number 2, how do you think the context problem could be solved? The application can save the tab history of how you got to the page, but then you would need to install a plugin and possibly send navigation info to an online service. Or you could add a note to the saved bookmark, but now it requires some of your time.
If other bookmarks were saved say 3 hours either side, show them in a slider style.
Granted, not every bookmark will be "next to" others, but it many cases this would give a good sense of context.
"Hmmmm a page on Google analytics... I wonder why I saved that.... oh yeah! That was just after bookmarking this page about 'Best tracking systems for WP blogs'"
Thx for the answer. Let me deep some more. Every month comes up a new bookmarking service with a very cool interface but it never get adoption and last less than a year. What exactly would make the difference for you?
I liked the suggestion by natch 27 for offline.
It doesn't have an offline feature despite have a browser plugin (I am not a huge fan of this).
In terms of interface I don't have a complete answer. I want to be able to have my bookmarks organized but a lot of the time I don't want to do it manually. Too often I bookmark something really cool but don't have to time to tag or comment on it so it disappears until I decide to organize my bookmarks which in and of itself is a pain.
Maybe somehow generate metadata/tags/etc from scraping the link or by what other people have to saw about said link? Of course this would be in addition to being able to comment/tag/etc yourself.
Thumbnails of the linked page would be nice, or if it was something from imgur for example, maybe the thumbnail is just the image that is on the page? I could go on but I think you might see where I am coming from; a lot of different features seem awesome but I think a lot of testing would be needed to see what people use and enjoy most.
I agree with you that user experience is important, but seeing so many alternatives that fail makes me wonder if maybe what is needed is a disruptive feature such offline access. Pinboard has everything you need to bookmark and is fast, pleople love it. However it does not have offline access to files and I wonder if that would make the difference for some people.