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I have never used the lighter socket cord, so this is just a wild guess, but the voltage would drop with more current flowing. resistance anywhere between the master buss and the cord will increase the current flow, possibly the iFly is more voltage sensitive than the Garmin unit is. I'd check and clean every connection from the back of the lighter socket to the circuit breaker, it the breaker is shared with other circuits. Both sides of the breaker if it's dedicated.
I could be way off base also though . . .
There has been lots of problems with the female jack on the IFlys . The male connector does not make a good ground inside the female jack. I consider it a poorly designed jack. I took my 740 apart and forced the ground lug to make a tighter fit on the male jack when inserted in the 740, and it has worked okay since.
I found that the internal spring on the power plug was so strong that any vibration on the panel would cause the plug to pop out out just enough to lose power. I replaced the spring with one that has a little bit less tension in it and fixed the proiblem.