Hi Kurtis,
First: what a mess of a task you have. Good luck!
OK, now to your problem: JPG is not a good choice for scanning for many reasons, here are two:
1) JPG is a lossy format. Lossy here means that the greater the compression, the more information it loses in making the image smaller in storage size. That affects the quality of the image in a way that is worse in high contrast images SUCH AS TEXT. It's less noticeable in photos of trees and grass, even people.
2) When you have a JPG image, you have to manually start the OCR process (an extra step), more on this in a second.
My general preference for scanning is to save the files in the TIF format. At first, this may seem bizarre because the image files are very large (storage size). However, after running the OCR process, the files are very reasonably sized (I've found the resultant PDF to be about .2% of the TIF file's size.)
The other advantage of TIF is that if you drag a TIF file onto the Acrobat icon, Acrobat will automatically convert the image into a PDF AND AUTOMATICALLY START THE OCR PROCESS. In addition, and this is important for you if you drag two or more TIF image files onto Acrobat, it will ask you if you want to combine all of the files into one PDF and then process the files with OCR while you sit and watch. It's all automatic.
Now, here's the one "catch": the OCR process is not fast, and to make things worse, Acrobat does not play nice with anything else you're doing while the OCR process is being done. So, if you try to read your email or check your FaceBook page, Acrobat will constantly bump itself in front of whatever you are looking at, letting you know that a page has been completed. Then the next page has been completed. (Etc.) So, plan accordingly.
One more bit of information: several years ago, I wrote the following blog for Adobe with many tips on getting the best quality scans for OCR. Newspapers are particularly nasty because of "bleed-through," where the text on the back of the paper shows up on the wrong side of a scan, which affects the quality of the OCR. (Note: you need to be signed in to your Adobe account to access this blog.)
https://community.adobe.com/t5/adobe-community-professionals/scanning-clean-searchable-pdfs/m-p/4785435?page=1#M89
Good luck!