Most of the existing error handling is in s3try.rb (not that it's necessarily where you need error handling added). Look for blocks like
begin
....
rescue Some::ErrorType => e
...
end
If you find where you are erroring out, and what error type(s) you have, you can wrap it in begin/rescue/end
What happened to your NAS? HD bork? I recommend spinrite for drive health (not affiliated, just a satisfied customer)
http://www.grc.com/sr/spinrite.htmDepending on the problem, you might even get to recover the old drive.