When Drive syncs with the local computer errors are often thrown indicating we may have reached the 256 character limit. In most cases this is not the case, we can confirm the length. Since we know the path to the starting character of the work area after the organization name could a system wide setting be made available to administrators to set what the actual number would be? We take the longest ProjectName/folder/filename length in ProjectWise and add the known length of the local computer path to calculate what it actually is, or at least a number that covers 90% of our staff as we have preset username lengths. This would avoid the error in Drive indicating the path is too long when it's not.
C:\Users\xxxxxx\ProjectWise\xxxxxx xxxxxxx\ (this is a common length for all staff).
Just a thought! This is a common problem.