Well, unless they have spatial references, the JPEG and PDF won't show up under the vector data because the software doesn't know how to project them. If you load the PDF up in Acrobat, can you use the Geo tools to show the coordinates and measure stuff?
I don't have the software here to see what I did, but I pressed some combination of buttons to reference it to nad83.
Like I said, My activity has been pretty unstructured. I've never used the software before, and no one in the office has either. I work with a bunch of dummies. The boss lives in the moment, and only knows what he's specifically been shown. He wants what he wants now, and thinking of better ways to do things doesn't even come to mind; adhd boy.
The draftsman knows what he knows, and if he doesn't know it, it doesn't exist. I've given up trying to explain anything technical to him. He'll tell me something related autocad, and I'll think "That doesn't sound right"(simply based on what a competent dev would do, and sane software design), then look it up, and find the correct answer. I know absolutely nothing about autocad, and I can intuit proper behavior. Him? Nope, can't be done.
The engineer is old and scared. He does good engineering work, but I think he'd be most comfortable with a sliderule and pencil. Like the draftsman, he knows what he knows on the computer, but he's willing and eager to learn if someone will show him. He's afraid of breaking stuff, so he won't try new things on his own.
All this is a long winded way of saying I'm on my own, and can't ask anyone for help. I can't even get a good answer of what would be a useful thing to have. Between the boss not thinking ahead, the draftsman saying it doesn't exist, and the engineer being afraid. I try to guess what's good, and try to make it happen. For me? All I need is my hp48 with a cogo program, and my gnu/linux desktop. I can do everything I need to do :^D