I've been reviewing my posts since I got a bit panicked about whether using CC images could land me in trouble. So I started replacing the pictures with my own shots, and reviewing the stories as I went.
If they're out of date and totally irrelevant, I delete. If they stopped earning 6 months ago and haven't been viewed on Medium since, I consider whether they might earn again if deleted and republished. I've done that with a few, but mostly they get improved or modified first.
There's no point keeping stories up that are out of date, if they're not earning. Unless you hope they might pick up a few cents in the future. They might. Old stories still get recommended from time to time. But if they're out of date or crap, do you actually WANT people reading them?