If doing a jump of 14/2 between the two speakers you now have three areas where the connection could go bad. Thinking of it at a troubleshooting standpoint you now have to determine whether the issue is at speaker 1, speaker 2, or the amp, which may require you to remove both speakers from the ceiling/wall to find the problem.

If doing a loop you know that it is a solid wire between the amp and speaker and only requires two areas of concern if needing to troubleshoot.

For us, troubleshooting is usually on our dime (depending on when the installation happened) so the faster it takes us to troubleshoot the system the more money we save.