(a) This can be solved with an editor. Alternatively, you can use a function name instead of `filename:linenumber` to set a breakpoint.

(b) Pdb supports conditions with `filename:lineno, statement`. Statement will have access to local scope. E.g.:

    $ python -m manage.py runserver
    (Pdb) break manage.py:11, os.environ["DJANGO_SETTINGS_MODULE"] == "myproj.settings"
    Breakpoint 1 at /Users/hcarvalhoalves/Projetos/myproj/manage.py:11
    (Pdb) break
    Num Type         Disp Enb   Where
    1   breakpoint   keep yes   at /Users/hcarvalhoalves/Projetos/myproj/manage.py:11
	stop only if os.environ["DJANGO_SETTINGS_MODULE"] == "myproj.settings"

Really, it does a bunch of things. I wonder why developers are unaware of it.

http://docs.python.org/2/library/pdb.html