[drone]

This x100.

Never use this style of connector/jack for supplying power. The cable tip will make contact with both the jack ring and sleeve in most jacks, and the cable ring will make contact with the jack sleeve. No matter how you wire the cable/jack, you always have the high probably of short on insertion/removal.

[marshray]

With electronics on both ends, the devices could easily negotiate in which direction power should flow, how much, and detect open and short conditions.

[drone]

So, tell us how you expect this task would be achieved. (I know some possible ways, but I could just as easily say "but none are as effective as using the right cable for the task!")