You can change that setting in Windows so that it no longer has a 255 character limit.

Yes, you can but then if you have any older software in your system (for company reasons) will not play ball. And it is a workaround, not a permanent solution. Because we still do not have that fabled WinFS so...

Eh, NTFS supported long paths since forever, the problem is with applications using Win32 APIs that are limited to MAX_PATH (260 characters) path length.

There won't be a permanent solution unless all Windows applications start using NT path formatting - which won't happen.

One drive still dies though

Win64 lacks the problem with 255 characters [0]. However, stuff like File Explorer, which the vast majority of my users actually use, can only pass the first 255 characters to the registered application [1], so will Explorer will display stuff with huge long paths, double-clicking that file, or right clicking and "Compress to..." will cause an error.

0 - 32 bit windows will always have this problem.

1 - This is because File Explorer uses a hodgepodge of Win32 and Win64 stuff behind the scenes when running 64 bit windows.