A real optimist. :shocked2:
I give it about 300' past the grate unassisted. After that I would think drag on the tether will stop it.
I'm betting there is no way this thing goes in unassisted. Unless it unspools line as it goes, divers will have to be in the water to keep the tether clear of obstacles and line traps.
I would probably suggesting dropping the whole coil of line at the entrance to the cave with 3-400' sections marked off on the tether and a diver assigned to each section. That would call for 4-5 divers in the water together with it, plus a couple of additional support divers for the deep team.
Should be interesting...