Yes I can see the value of reposting older submission, I think my main discomfort is having to add random characters to the urls in order to fool the dup detector so that people can post an old article again.
If the community agrees there is value in reposting old articles, maybe change the dupe detector to allow reposting old articles after N days. Since that would become part of the system (instead of working around it), it would become easier to link old and new submissions for example...
I just don't like it when one has to work against the system to do something if the community seems to feel that something is worth doing.