Is there any way to make the ropes connect properly? I also intend for the crane to (appear to) move vertically instead of horizontally, so how could I make that work with props?
There's probably a prop or brush that connects them in the map, or there may be a seperate version of each piece. As for making it move, set it to a prop_dynamic and set it's parent to a func_tracktrain. Here's the dev wiki page for track trains https://developer.valvesoftware.com/wiki/Func_tracktrain, and here's a tutorial on this site http://tf2maps.net/threads/tutorial-trains-the-easy-way.11495/.
That's not the prop set you're looking for. I mean, just look at this: The prop at the top is definitely different. Plus, the platform looks physically unrealistic if it's hanging in mid-air.
You could probably try to put some ropes (move_rope, keyframe_rope) in the air between the models' ropes.
Actually they look like the same prop, only with extra little crane props attached. Incidentally, if you're having trouble recreating that prop setup by yourself, you can always download the decompiled version of Well and copy-paste the point into your own map. Trust me, no-one will mind.
