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Thanks. I've decided to update them and maybe try for some easier keywords in the headings as you said.I would not delete those posts. Some posts are good just to have as a 'base'. You can refer to those posts from other articles.
Maybe you cannot rank for the main keyword, but it is probably possible to address some long-tails in the H2's. You can try to rank the article on those long tails. To support the 'difficult to rank posts' you can also write separate articles on those long-tails and link back to the main article. Who knows, maybe you can rank in the future.