Webform questions

Hi,

Love your videos, its the first place I use for resources for my problem.

I have 2 webform questions:

question 1: Is is possible to have a webform that will allow a visitor to upload an image or file (PDF or text doc) and have that get included in the email as an attachment?

question 2: can a webform field(s) populate another webform field? After they click submit it just populates field in another form. Or is this better for a custom content type somehow? But it needs to get emailed in the 2nd form, so thought of a webform.

thanks!