I think we got ourselves into trouble on a site many years back with 301 "re direct chains" introduced through indecisions about where content should sit . e.g. A > B > C > A
The site dropped out of the rankings - indeed it was nowhere to be found even though pages were cached. After several years the site came back slowly , although it's not fully indexed.
From Matt's remark's he says that Google will at some point stop following the redirect. But is there an issue with " trust " as well ?