The answer to your first question is no. The internet is ephemeral and things shut down, move, or get deleted all the time. If a third of your links are doing this, you need to be linking to larger, more permanent sites, though.
The best link maintenance tool I know of at WP.com is the randomizer button. I use it on my own blog to bring up random old posts, on which I fix the links if any are broken.
Permalink just means the permanent web address of that content, but it’s not a guarantee of permanence at all. That’s up to the webmaster at those other sites.
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