I havent experienced this issue in a while. I leave an update if I get to encounter this issue.

I have seen some other people experiencing this issue especially when encountering Error Domain=kCLErrorDomain Code=0 "(null)" The error supposedly a normal behavior but the actual behavior is that it stops call for didEnterRegion..... This is a serious problem for certain app developers and users. I really don't post question but I just cannot find a way to troubleshoot this issue.