Sure. Like most diving procedures, there are tradeoffs, and you can always come up with scenarios that favor one or the other. And the decision on how to ascend would be based on a number of things, such as the specifics of who the OOA diver was, what their experience, training, and assessed mental state were at the time of rescue.
However, you are assuming that I was suggesting just handing off the bottle and leaving. I didn't say that. I just meant that if you are ascending it's better if you are on your own back gas.
There is nothing to prevent you from ascending with the OOA diver and doing all of the things that you mention, but a regulator isn't a good means of keeping two divers together. If the OOA diver is breathing off the pony, then no matter what happens he will have gas. If he is breathing off of your short primary hose, then there is a chance that you could get separated (surge, current, panic) and then he would have NO gas. Which is always going to be worse than any of your scenarios.
Finally, there is the possibility that he will become SO panicked that he will put you as the rescuer in danger. And in that case, it might be good to be able to break free without depriving him of his gas supply.
If I was diving OC and had to rescue an OOA diver with only one second stage and one pony bottle, I would do this:
1) Plug my primary into the OOA diver immediately.
2) Deploy my pony and breathe off of that.
3) Once the situation was stabilized, try to get the OOA diver to take the pony regulator
4) Unclip the pony and clip it on to one if his D-rings
5) Make a slow, safe ascent together with a safety stop as planned.