Weeeelll...
It could work. You'd have to plan around weather to avoid operational disruption (diversions) due to inability to get or remain connected. They could set some operationally (economically) tolerable threshold above which it gets too costly on average to risk diversions.
Obviously the real risk is collision but maintaining a formation flight is actually something which automation *should* be able to do better than humans... simple task, which requires unwavering attention.
If you absolutely have to power long-haul planes with batteries, this is probably the only way it could work. I guess there's ground-based laser power beaming, if you don't mind toasting the odd bald eagle or CE-172 that gets in the way.