It would be as hard as writing the file {n} number of times again. So if one created a 1MB log file and then did a 3 pass wipe that would write 3MB. Number of passes would really just depend on the system being worked on. If PCI I would expect 7 passes and I am sure that would just be factored into the cost of the servers for that environment.
Shred also isn't perfect as it has no concept of the file systems journal and does not clean that data but I think it is still good practice for sensitive data, in addition to filesystem or file level encryption on systems with highly sensitive data.
With sensitive data one must look at the value of the data vs the value of the SSD. If I go out of my way to extend the life of my SSD, do I risk losing $5billion? That is how I factor in whether or not extra wear-and-tear on a SSD makes sense.