Hi William,
This sounds like an excellent area to automate the boring stuff. I recommend writing a script to iterate through the features using a cursor, and then for each feature download the image, and add it as an attachment for its corresponding job. I'm not sure how you have the hyperlinks stored, but parsing job information and adding the attachment can be handled using our module. I recommend taking a look at the job class for adding the attachment, and whichever class corresponds with how you have the information stored. Here are some recommendations for downloading the images. I hope this gets you up and running!
Thanks,
Sam