You're right, I've thought of the "self-enforcing" thing. To try to combat that, I run reposts as well from back when my blog was young and not that popular and I do a "most popular posts of the past 30 days" post as well and often those old posts will show up.
It's amazing that I re-run posts (always full disclosure that is what I'm doing) and both new readers and old readers will say thanks. I have one post that I think is number 5 of how many times it's been run. And each time it gets a lot of comments.
I even wrote a post about reruns and asked regular readers what they thought and they all like it. My regular readers also tend to provide links to their favorite posts. With a self-help blog, that's easy to do. If your blog was about current events, I suppose that might be hard. :)
I do like the selection of my own links idea.