Well, I've broken the ice that formed on my project over the holidays. There's something that really intimidated me about going back to that code, that work flow. I don't know how to explain it except that I felt afraid of my own code and lack of experience, felt like I wasn't going to remember anything. So I hemmed and hawed but tonight I got back into it for a solid 3 hours and it feels good to remember what I was doing and why.
One small change that has made my life easier - I added srctool.exe to my path so I could call it from anywhere and this makes life good because when I want to test if my code is working I have to call make on the new symbolstore.py, then call make buildsymbols in my objdir, then go into the command window and call srctool.exe -r (a raw dump of the indexing info in a pdb) to see if it all worked. The path to a pdb file is something like C:\ff_clean\mozilla\objdir_debugInfo\dist\crashreporter-symbols\2007120422\accessiblemarshal.pdb\E82E8047412045539226FBBC0BE301974\accessiblemarshal.pdb
and so being able to go to that directory and just call srctool -r accessiblemarshal.pdb is way easier. So I'm happy about that.
I've submitted my changes so far back to the bug and am now awaiting feedback. If I can successfully handle at least one of the points that led to a - review, then I am moving forward.
Now it's time for some (light) reading about windows proprietary debug database formats.