I've got a general directory that's about 8 years old, pr2. 32K pages of listings, an obscene amount of dead links All the pages are static html (long story). Haven't touched the site in years. It still takes traffic though, on some really out there long tail search terms. Domain name isn't bad either, it's search related.
Is there any point in doing something with the site in the way of monetization? Something relatively easy? Or is this a waste of time?
Looks like you either auction it off "as is" or find a way to srcape its contents into a database version of the directory, one that maintains the same URL structure, and then extract the bad links. That latter idea sounds like work, the ROI of which only you can best project. You might need/want to outsource the "manual labor" to get a better return.
When it comes to making money online diversification of income streams is gospel, so I'd consider keeping it if you can repair the situation to profitability with aff links, contextual ads, listings, etc.