Advice: Massive Grateful Dead Metadata Project

You can retrieve data from the filename (and that includes the path) with Converter>Filename-Tag.
The Converter only works if the pattern that you supplied matches the pattern in the (complete) filename. Otherwise not data is transferred.

There is a fairly sophisticated filter function in MP3tag that allows to use plain words or more complicated patterns.
I would use that to narrow down the files that have a common pattern in the filename and that can be treated by the same converter mask.

You would definitely have to work in steps to treat all the variations.

I also would first of all get the raw data into clearly identifiable fields, even if the data is not yet quite up to standard - and then treat these fields with special actions which (I think) is easier with structured data in fields than unstructured data in the filename string.
I strongly recommend a look at the FAQs on the converter function.
Once you get some data into the fields or fail to get any at all, come back here and ask specific questions.