Yikes, 260 character path names can be a real pain. Please support sensible path names or at least tell me why you can't read or write to a file. Often you just get a "can't write to that file" error message, or worse, "forbidden" so you spend an hour trying to debug the mess that is folder permissions on windows.
I'm not going to convince you to change your tool chain, userbinator, but for the sake of the discussion: Once you have multiple projects going on, with multiple components, and then those components have a small directory structure themselves, you can easily reach 260 characters. Add to that, if theres data coming from another org, a long file name can be very helpful to keep track of what it is (and don't forget 10-12 characters for a date!). And finally, the nail in the coffin: most users don't think about path names, I struggle to get people to not put periods in their filenames which messes with some tooling, how am I going to convince the guy in finance who gave me this data that he should use short file names? Should I modify the file name and make it untracable?
ETA: The "if you have to ask you've messed up", I don't ask, I expect and then get annoyed it broke. I had 10,000 files collected into a folder. Why can every other program tell me the list of files in an instant but windows explorer crashes (the whole desktop environment) because I opened that folder to see it. I'm not meant to do that? Then why can the kernel, the disk, the file system, and all other programs handle it with ease?