Required Field through Drop Down UDT

Trying to brainstorm possible options for this specific problem we have.  In our business we have file names for embroidered logos (roughly 50k files maybe more), right now users have free range on if they type a file name in the description field of a misc item code.  The misc item code is used so we can bring up a template of possible locations that can be embroidered and the user just fills out the template with information.  If the user enters the file name for "EMB" it allows the operator (person who decorates the garment) to go straight to the file on the computer and pull it up.  Some users might just enter the file name ie " (SAGE) this would indicate a logo for SAGE on the left chest" or " (SAGE.EMB) same meaning they just included the file extension which we want them to start doing", either way works but we want consistence.  If a user doesn't enter/type a file name in the description the operator has to go "hunt" the user down and ask them which logo to embroider, taking away productivity. 

Now to my thought process, I've read making a field required could cause more issues than it's benefit, so I thought about (not sure how it would work) making a UDT and creating a drop down menu for users to select the file name in the UDT.  The field would be required, done by scripting, only if the specific misc item code was selected for embroidery.  Issues are the files are not broken down by customer, so the drop down could possibly be 50k options.  We could breakdown the files by customer, it would be some work, but then we would have to create a UDT for each customer.  I have reviewed the embrodiery files DB and it looks similar to SQL, which could mean linking the DB's.  In SAGE can you display PDF's in lines via drop downs?