ugh, ownership problems... I had these too

I think it's because the different users/groups are identified by GUID. Once you reinstall the OS, your new user will be assigned another GUID (randomly). Also, the OS has no way of knowing whose username corresponds to the old files owner (if you look at the permissions you'll only see the GUID, {42ECAF20-334A-1069-A2DD-18232FAF309F} or something similar) because the old users aren't stored anywhere anymore. So even if you name your new user the same way you named your user in the previous OS, the OS has no way of knowing that. I have no idea if I made any sense with my explanation.
TL;DR version: I think you can solve this problem by setting "Administrators" as the owner and deleting everything else listed there that isn't a default user account/group.