I’m one of the airline pilots on the boards. The short answer is “almost certainly not”.
Certainly it’d be impossible without extensive modifications to the aircraft involved. But could you purpose-build a transfer mechanism and fly it sucessfully? Well maybe. Just bring money (lots of it).
At 30,000’ the air temperature is roughly -45C or -50F, i.e. seriously Arctic.
The cruise speed of a typical jet airliner or militray cargo plane at that altitude is about 500 statute miles per hour, but the thinner air up there results in a wind blast whose pressure is the same as about 300 mph at sea level. i.e. it “feels” just like a 300 mph wind. For comparison’s sake, that’s the same as an F-5/F-6 tornado.
About the slowest such a plane could safely fly at that altitiude is maybe 250 mph of sea-level equivalent wind. A mere F-4 tornado.
Doing anything involving a person in a severe tornado in the Arctic sounds pretty challenging.
Aerial refueling is a similar task to aerial personal transfer, so let’s talk about that a bit.
The USAF does aerial refueling at those speeds all the time. Keeping the two aircraft relatively stationary to within a couple of feet is not difficult, provided you’ve practiced it a lot. It does take your total attention though.
The USAF method has the receiving aircraft slide in behind and beneath the sending aircraft. Then a rigid pipe about 8" in diameter is lowered towards a 2-foot square funnel set in the top of the receiving aircraft. The pipe has small wings on it and has a hydraulicly-driven extension on the end.
The sending plane flies perfectly straight, normally using the autopilot to ensure precise control. The receiveing plane slides in behind/below the sender and the human pilot does his/her best to hold absolutely still. That gets tough in turbulence, as well as the fact that the sending aircraft is always trailing a hellacious wake as well as violently disturbed air flowing out of each engine.
Once the two airplanes settle down, a crewman (the “boomer”), looks out his window in the rear belly of the sender and steers the end of the probe to just outside the funnel, then extends the probe to stuff the end into the funnel. The funnel mechanically latches the two aircraft together and fuel can then be transfered. The boom has a range of left/right and up/down motion, as well as in/out via the extension that requires the receiver to remain within about a 5-foot radius sphere around the center point. That’s usually doable for the several minutes required to pump the gas. In vile weather or if the receiving crew is tired, it can take several tries to get this done.
The Navy (naturally) uses a different system. The sending aircraft trails 50-75 feet of flexible hose off a reel just like a firehose. At the end is a “basket”, which looks like a badminton shuttlecock made of heavy nylon webbing. I’ts about 2 feet long and 18" in diameter, with a spring in its rim to hold it open. The wind blast keeps the hose more-or-less taught and the basket is aerodynamic enough that it stays more or less still.
The receiving aircraft has a rigid pipe (“probe”) sticking out the front. The receiving pilot’s job is to drive up and plug the probe into the basket. There’s a suitable connector at the center which mechanically latches onto the end of the probe and fuel can then transfer. In any kind of turbulence or weather the basket can be jumping around in large circles and be very hard to stick.
If the basket gets damaged so it’s not perfectly symmetrical, it skitters around on the end of the hose like crazy and is totally unusable. It’s too dangerous to get near a damaged basket; it can easily punch a hole in the receiving aircraft’s fuselage or break open the canopy/windscreen. Ouch!
The Navy method only works because both the sending and recieving aircraft are relatively small fighter-types, not lumbering transports like the USAF method was designed to support. So the wake from the former isn’t tossing the basket too much, and the latter is manueverable enough to hit the moving target.
OK, now let’s go back to people. One thing a person is NOT is aerodynamic. So if we hook them on to a rope and start lowering them from a door near the back of the plane, they’ll be skittering all over the sky. Unless they’re wearing an oxygen mask they’ll pass out in seconds. And unless they’re inside some pretty amazing clothing their limbs will freeze to unusability in seconds.
Before they freeze they’re probably not strong enough to hold their limbs against the wind blast to steer like sport parachutists do. And near the sending aircraft the airflow is a random tornado of swirling air. Imagine the most amazing white-water river you’ve ever seen, but it’s invisible and moves in three dimensions. Now imagine trying to surf that.
So now the receiving pilot slides up near this madly flailing body on a string, looking sorta like the sports-team flags you see on cars, whipping madly as they cruise down Main Street.
As they close on the guy, eventually he gets whipped into the side of the receiving plane and breaks at least one bone, more likely most of them.
So, that ain’t gonna work. Time for plan B.
I could imagine building a small capsule, say the size of a household garbage can, and using a variation of the USAF method. The can is attached to the end of the boom and is plugged into a suitable recetacle built into the top of the receiver.
But it wouldn’t be easy. You’d have to have a way to nest the capsule against the underside of the sender and provide suitable hatches so the person could get in, and also provide an airlock of sorts at the receiving end.
Possible, yeah probably. Sensible. No way. Like I said at the start, just bring money. Lots of it.