I would vote for allowing the "Pit stop" idea! The reason is that I see trackable items listed inside of virtual and Nano caches that obviously don't fit. I really like trackable items. If it is stated as being in a cache, then it should be there. So if we allowed trackable items to only "Pit stop" in certain kinds of caches, then we could eliminate those stragglers that get left in caches that can't physically fit there.
This is how it should work:
Trackables could only be "Pit stop"ed in any caches, virtual, or earth cache if you actually visit the site, (i.e., found log).
When logging the Trackable, you would be given the choice to drop, or "Pit stop" the trackable.
The cache page would be unaffected by a "Pit stop"
The trackable page would show the "Pit stop" similar to a discovery with a link to the cache page and log the miles to that cache under miles traveled.
The user should be automatically taken to the log of the trackable "Pit stop" after posting the find to add comments to the trackables page. (This could prevent the blank entry's of dropping trackables too!)
Trackables would NOT be allowed to be dropped to stay in Nano, Virtual, or Earth Caches!
I have seen trackable caches designed for the purpose of "electronically" housing trackables, (I don't personally get this) but these should clearly be identified for this purpose and not use the virtual or nano cache identifiers.
I think that this is a good compromise and will also help to clean up the site.