@abrown8 -
As to what @Chris_Hofer mentioned - it is not too bad to move items around in a module with drag -n- drop unless you have more items than are displayed at one time on a page.
However, I am not sure, but if you do a bulk add of assignments to the module, they may be added alphabetically - I have never paid attention to it. Of course for selection, the items are alphabetical. Or, as is usually the case my items are alphabetical to begin with. If you are adding the items one at a time, then just add them in the order you want them to appear. I am not sure about dragging and dropping the files in with the initial setup.
You may have to play around with adding content to see what is happening so that you can figure out the way you want to add items to the module to minimize the amount of sorting work that you need to do.
I just tried adding in quizzes that showed alphabetical, but when I added a group to the module the placement was random. I checked the due dates and none of them had due dates, so that was not it either. I thought it might be the id of the assignment for the initial ordering, but that is not the case either.
Sorry I can't be of much help in explaining what is happening