I am sure to some people, this is pretty easy to follow. But this makes no sense to me.
Using your Option 1 (We simply want an attached file emailed to the customer, not saved on a server).
Here is what I did:
I selected the form in DW, went into the Edit Form in the Properties window.
Clicked on the Form Function widow in the CSS Form Builder Wizard.
Edited the Send Mail Settings.
Clicked on the Paper Clip.
From there, I Added a Type and selected the Submitted File radio button.
This is where you lose me. It doesn't allow me to edit the value to place the cursor before the server file name. Even if it did, what am I suppose to paste?
Where would I check to make sure I'm using the correct work flow? It seems that if I select the File Upload option in the wizard, it should be much easier than this. I did look for instructions on how to do this, but was unable to find anything.