I think the answer to my second question is no, they have to be unique names. I'll have to unique the file names based on my Field's document ID for each record. Something like this:
"field-ABCDEF123456:Canadian Flag.png"
"field-ABCDEF123456:USA Flag.png"
"field-ABCDEF123456:British Flag.png"
and then even another set for a different field:
"field-XYZDEF123456:Canadian Flag.png"
"field-XYZDEF123456:USA Flag.png"
"field-XYZDEF123456:British Flag.png"
Even though the file names after the : are the same, they may be different files within the same record. For example, a smaller and larger version of the same file or even two different styles.
Then if the user deletes the file attachment Field object from their form, I can search all records for any attachments with names that start with that field's document id "field-ABCDEF123456" (or whatever) and delete the actual file. And I guess if they delete the record itself then CBL would handle deleting all the attachments for that record by itself I think.
Sorry if I'm spamming the list. Hopefully these questions are useful to others too. I don't have anyone else to work these things out and I find this helps just to type it out.
Thanks!
Brendan