First, I think too often there needs to be a clarification as to if you are up against rivets
or screws
Rivets are almost always smooth headed most semi trailers, semis, box truck boxes, are put together with rivets. You do not want to try to remove these! Although many many times I have used both regular calendered or cast cut vinyl over rivets. They are difficult but with experience and a little fineness you can get them to work out fairly decent.
If I'm doing a large enough job to justify it, the best you can do is use some version of an air release vinyl.
On most enclosed race car / landscaping type tag behind or 5th wheel type trailers the panels are attached with the kind of screws shown here. They are an 8 point screw that a #2 square bit will fit. I always remove these / apply the vinyl then reinstall the screws.
One tip is to remove all the screws in the area of the install / clean /start applying vinyl, after you finish applying an area reinstall the screws in that area to help stabilize the surrounding panels. Some trailer manufactures secure the panels to the frame (before screwing them) better than others.
Also, as a side note, if I'm involved early enough in the process of a customer getting a new trailer built, I suggest a screw-less option. It's not much of a cost increase, they look tons better without all the screws, and the customer will save money on your end because the vinyl install will be cheaper.
Sorry for the long winded post but I see / hear this (not knowing the difference between screws or rivets) out of customers and newbies to this biz all the time.
Hope this help someone.
Jeff