The thing that comes to mind immediately is that this would create an exponential explosion in testing complexity. I am not saying that the end goal is not laudable, but that the number of tests that would need to be run is the product of (well, in round numbers):
- the number of versions for each dependent module,
- the number of versions for each child dependency for your dependent modules,
- and so on throughout the dependency graph.
The best compromise I have come up with (by no means assume that I should be an authority on this) is to test at the latest, and include exceptions in your Build.PL, Makefile.PL, or META files. If you require specifying a full dependency chain, then test with a specific set of dependencies, and use the CPAN toolset to lock that configuration down in your environment.