Youme makes the good point that the devs have admitted they tried to dumb down the skill level for the game. While I will not get into that argument, i would point out that these maps are based on a skill. Admittedly it is not a skill that TF2 requires a whole lot, but it is a skill nonetheless.
Yeah the idea i suppose would be to have stages with a cp at the end of each one. For the sake of discussion say you have 3 jumps/obstacles per stage. If you fall on the second or third obstacle youd have to run back to the first one and start again. Once your team gets past the 3rd obstacle youd open the next stage and obstacles four through six. Falling here you run back to obstacle four and start over.
While death might make people more nervous about failing, you could also make the falling be a double penalty by creating some semi-difficult jumps to get back up to the top. Probably the ideal though would be to mix it up. Have death be the penalty in some places and a run back in others.
As for the moving spawnpoints, I am virtually certain that is easily done. It is essentially analogous to having advanced spawns in well or granary. I am not sure of the particulars, i imagine it has something to do with disabling the original spawn points and enabling new ones further up. I'd have to look it up but I imagine the information is readily available.
To return to my Pyro idea, this concept was brought up by jive in my control point post (
http://tf2maps.net/showthread.php?t=695) in which he suggests using a "prop_physics_multiplayer" entity that has an OnIgnite command. You would also need to put down a spawnroom brush so that people could change classes without dying. So here would be my scenario:
The player has just gotten past another obstacle to a platform. On the next platform up there is a cp which he can easily reach by a scout or rocket jump. However, the CP is surrounded by a structure that cannot be blown up, it can only be "melted." Either the platform or the CP would need some kinda hint as to what you need to do (i.e. become a pyro and burn the structure to access the CP.) That way you force the player to do some jumping with one of the non-special jump classes.
Would be hilarious if we could somehow filter for the HWG's minigun fire so that people would have to switch to the fat man and try and make the jumps. Alas, that cannot be, yet.