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Yes, it's a known problem. It was discussed a couple of times last year. One of the reports hit a problem with about 3000 books. But, I think that was with a 1.9.x firmware version.
With the last few firmware versions, it isn't a problem for the SD card user. The cover images aren't stored at all. It also isn't quite as bad with the 2.x.x firmware. The 1.9.x firmware generated four cover images when a book was sideloaded. 2.x.x generates them as needed and only generates three (one for the home screen and sleep cover, one for the library lists and one for the details page).
Changing the calibre save template is a simple way to slow down reaching the limit. The default is "{author_sort}/{title} - {authors}", so changing to "{author_sort}/{title}" would reduce the length of the name a lot without losing much info in the name.
An alternative would be to rename the image files and update the database to match. Dropping "file..." prefix would save a bit. That wouldn't be to hard to automate. Or maybe a database trigger on insert?
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