Probably this is a bit of a noob question, but... Is there any way to upload multiple files with the same name into the same library without use of folders (which are evil in SP :) )? My understanding is that this is not possible, but maybe I can do it if I somehow leverage some other unique column which SP will take into account along with file name so that name match won't present an issue?
Short answer, no.
If you have versioning disabled in the document library, the new file will replace the old.
If you have versioning enabled in the document library, the new file will be added as a version of the old.
You could develop an
item adding event receiver that checks the file name and changes it if duplicates are found, but I don't think this is what you're looking for.