As always, pkg_rolling-replace is unlikely relevant. Please reduce to a situation with no workdirs, and then make replace. (Unless the issue is that you have pyNN-foo with non-default NN.)
It seems it's a typo (quotes) in www/py-urllib3/Makefile. Fixed, and problem isn't happening any longer.
Yes, pkg_rolling-replace works well, in my experience, and lately I can count on it more reliably to run unattended.
Thanks, John