Think of the Yahoo Directory.   It has cost associated with it and a listing there indicates a real website rather than spam.  Whether no-follow or not, if a directory carries trust and authority it is beneficial.

Regardless of what is said, these listings do add to your metric profile and do contribute to ranking.  Just like all the other "non-working" link types (read Press Release etc).

Don't believe me?  Go disavow or remove all your no follows.

I would create a piece of content for the head term and call it the mom.  Then I would create many children with each child targeting a tail set of synonyms referencing  the mother.

These children would live on the target site as well as related topical sites and web 2.0 properties.

Mom and children alike would get pretty and all dressed up with table of content's style interlinking to encourage user engagement and long click like activity, especially on the target site.

Long story short is that both are important and if the content is good you will receive tiered social signals and linking naturally via this practice.

That said... I am a very big proponent of increased site production and if I had to choose one over the other I would take fresh topical content with proper interlinking on my site any day as it means new ranking opportunity, user engagement and almost always new traffic.