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Page A has two links on it that both point to Page B. Link 1 isn't no-follow, but Link 2 is. Will Page A pass any juice to Page B?

I'm curious about links that are just URLs (e.g. http://www.google.com/reader) or in a URL-like format (e.g. Google.com/Reader) vs links with plain-word anchor text (e.g. Google Reader). If a link that is just a URL (or a partial URL) has keywords in it, do those keywords provide anchor text relevance benefits? I'm particularly thinking about URL shorteners that provide customized links, and social media. Many web tools (twitter, blog comment systems) don't render HTML but will automatically link URLs. If http://boston.craigslist.org/jjj/ gets linked to through custom shortened URLs like http://bit.ly/Boston-Jobs, is it more likely to rank for the term "Boston Jobs" than if it received the same number of links using a non-custom shortened URL like http://bit.ly/ejq5uX9?

My understanding of domain authority is that the more links pointing to any page / resource on a domain, the greater the overall domain authority (and weight passed from outbound links on the domain) is. Because URL shorteners create links on their own domain that redirect to an off-domain page but link "to" an on-domain URL, are they gaining domain authority each time someone publishes a shortened link from their service? Or does Google penalize these sites specifically, or links that redirect in general? Or am I missing something else?