edit, it's been a long day, i got confused.
if you want, have your roofer guy check out Aerial Sketch by Xactimate, http://www.xactware.com/en-us/soluti...aerial-sketch/
and Eagleview. http://www.eagleview.com/
those will probably save him some time in the field estimating.
as for the forms, i dunno, probably some custom thing the other guys had written. Adobe might offer something for the forms and digitally signing them, but the auto-upload as a single package is outside my sphere of familiarity with anything i've worked with.
you might call that competitor as a 'sales guy' cold call and offer services, when they deny you, inquire about what software they're using currently and ask about their satisfaction level with it.