Gotta love how the sentries in the movies have crap aim, where as in the real game they just about can't miss. And that heavy was a noob, how did he not rip the scout's head off when he had him in a headlock?
#5 would be possible, as long as you had someone you were charging that knew what they were doing. Maybe Duel_Duel2 would work for that, people will usually listen to a plan when the alternative is dying as soon as they set foot outside the door, and that plan usually involves a medic and an ubercharge, usually with a soldier charging it up quickly. If it doesn't work on custom maps, though, you would just need to have a friend playing your uber-buddy, soldiers work decently for uber targets, just make sure they have four rockets ready before charging, they will likely go through that and the shotgun, might even start trying to hit people with the shovel. You would get at least five kills in the three charges, though. Heavy would work well, obviously, and pyro might, you would have to tell him to burn his targets enough they would die before the uber ran out and you two died. Usually when I am an ubered pyro, I just try to light as many on fire as I can, push them back. I usually get a couple kills, but some of those come after I am already respawned.
#1 would be difficult, but I would put it under the needs luck.
#27 would just be camping healing a sniper way back in a match where your team is having no trouble. Or, alternately, in Duel_Duel2, standing by the medic cabinet while your ally shoots out of the door, any splash gets healed up by the cabinet, but make sure you can't be seen from the door, or you will likely get killed. Again, that depends on whether you can get achievements on custom maps.