I have done both: probe drogue in the F-100 numerous times, and flying boom into receptacle in A-10 and F-16. Only once, off a RAF Victor tanker, did i hook up onto a flailing 50' hose, successfully. AAR is not that hard: fly formation off the tanker, watch the up down, in-out lights on the belly, and make microscopic corrections of throttle and stick. My first boom AAR was at night in the A-10: the receptacle is directly in front of the cockpit. Interesting....
When going overseas, you refuel off the accompanying tanker constantly. You need enough fuel in the jet to divert to the nearest 8000' of concrete with arresting gear. The longest overwater leg anywhere is Hawaii to US, 2500nm with no islands in between.
The video of the LSO in driving rain is great: I have respect for any aviator that can trap, anywhere!