In order to use Steam at all in offline mode, you need to tick the 'Remember password' box so it can log in. (I think, please do try it and see if it works). If that doesn't solve it, then I don't know. Sorry.
They may have just glitched or you must have harmed them somehow. You could try reverting back to a previous save, if that helps. This has never happened to me before.
I guess Skyrim doesn't have that ability anymore is because they want you to actually do the picking, rather than just relying on the auto-attempt all of the time. That damn skeleton key.
Oh dear. It is cool to explore things, but without the ability to fast travel, in certain places, it can get quite tedious. Anyway, good luck with your endevours!
I would love to see Bethesda to expand on the landmass seen outside of the games boundaries found by that one guy. It would be pretty neat, don't know how it would work though.