Since we weren't there it's hard to say, but my rule of thumb is that if I'm even considering taking my foot off the gas then it's almost always time to do it. Playing and beating
up on a bad team doesn't help you in the next game.
Then only exception is that in leagues with 5 run limits like you have. It the pitcher is just walking kids around the base you might as well go on WP''s to get it over quickly. If the pitcher is throwing strikes let you kids have some fun and hit. However even then I would only go on WP's (PB's) and stop stealing and certainly stop doing any form of delayed stealing.
It wasn't a matter of stealing...or running on wild pitches...we weren't doing that...it was a matter of the assistant throwing up the stop sign on big hits to the outfield. I guess part of me hates seeing one of my players hit a bomb to the outfield being stopped at first base.
To be honest I have been on the other side of that many times and I seen teams not run on overthrows and stop stealing, but an have never had a team go base to base on me. So I really didn't know that I was breaking any unwritten rule. I have coached for four seasons but I still consider myself a green horn.