If it were me, I would ask them to explore the possibility of cleaning up the existing caulk, and treating the whole thing with "Eternabond"; right over top the old caulk. It would be a LOT less labor (it's hard and very tedious to remove all that old caulk without destroying the roof), but more expensive in materials, and the repair would basically be permanent.
If the roof membrane is in good shape, this could be a much better alternative, and may even be cheaper.
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