Hi Michael,

I'm not sure I understand your question. Are you trying to add hyperlinks in ArcMap? To do this, you could either add a field in the parcels layer with the urls or create a gdb table from your .dbf and join that to your parcel layer.

What hyperlink files do you want to populate with a script?

Try the Python forum your Python specific questions. Thats probably the most active forum and you'll get a lot more eyes on it there.