Thanks for posting the Action. I will setup something similar here to see if I can recreate as well. The Conditions are a little different from the Action that was determined to be failing at 02.06 so it could be another variant but I did not think the Conditions were causing the problem. If the telnet trace covers a few days it will likely be too big to post. Send it to the same email you have been using.
You might try reversing the Effects, putting the X10 Effect second, or adding a 1 or 2 second delay to the Insteon Effect. I have nothing to know the combination is a problem but the PLM does not buffer commands. If there is a timing issue between X10 and Insteon commands causing an intermittant rejection of one of the Effects it might affect reenabling the Action.