I think the power is not as much of an issue, I guess I just get "spooked" when a common ground is not maintained. I know that I'm not interested in sending logic signals across without ground.
This may be more of an issue with TMCC as the logic signals are indeed returned to frame ground, and the scenario I mentioned would certainly put the electronics at risk. With all the cautions about not grounding lines from the PS/2 package, I just figure that having a consistent ground can't be a bad thing.
I've seen the MTH stuff both ways, with rollers just on the locomotive, and rollers just on the tender. Again, I'm not as worried about the power, and if I were going to steal a signal line, that would probably be a candidate.
As you say, another consideration is getting a good ground on the tender as you don't have the extra contact of the locomotive wheels.
Perhaps I've just designed too much aerospace stuff, they'd turn over in their grave if I suggested such an arrangement.