Is there a way to reapply plastic to locking screws where the plastic comes off or should I not bother? I am not sure how well it works at this point?
The pre-applied “nylon patch” is designed for only a couple assembly/reassembly steps. Fasteners like this are used in industry a lot so that assembly personnel don’t have to fool around with a bottle of liquid threadlocker. When I worked for La-Z-Boy, we specified these screws all the time for the mechanism assembly.
The alternative, where locking screws are needed, is to use “Locktite” ™ or a similar threadlocker. Be sure to get “medium strength” or you won’t get the screws apart. Here’s a recommended source for all kinds of hardware (and other tools and supplies): https://www.robosource.net/thread-lock-tape/181-thread-lock-blue.html
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If you are applying threadlocker to screws, I vastly prefer the “gluestick” style Loctite 248 over the liquid Loctite style. Even though it’s a bit more expensive, you won’t waste it constantly when students spill or overuse the liquid type. 
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It’s easy to remember