Hi garriew,
so what you say is, you used the above structure, but it didn't use proper file due to naming?
That is possible, for such cases (nested groups) we had done following approach (sorry, not yet documented in wiki ...):
Replace the backslash with a dot.
There is an example in the samplemovies db:
"Harry Potter.Harry Potter and the Deathly Hallows.jpg"
That one will show as group/collection image forHarry Potter\Harry Potter and the Deathly Hallows\<movie titles>
So in your above case you could use (and those should be properly assigned):
A-Team.Season 1.jpg
A-Team.Season 2.jpg
Buffy.Season 1.jpg
Buffy.Season 2.jpg
We might also add the logic to get the thumbs from nested pathes, but I thought that is not so nice, as it would require a lot ob subdirectories...