So after lots of trial and error with an eval license, I finally figured out that if I disable cache, things seem to work fine.
But if enable cache drive(s), it fails to move the files and I get timeouts after about 4 hours of copying files to the array. It happens with both SATA Spinning Drives and SATA SSD drives in the cache (or a mix).
I tried with multiple drives, and then dropped down to single drive to see if the issue kept happening.
Once i disabled the cache completely, the issues I had stopped.