it would have to be 8oz distillate to hit 2000mg per tsp, but I guess that doesn’t really answer your question.
The cannabinoids will mix with the oil at every ratio, so there isn’t a limit, so much as a most efficient amount of oil per amount of bud. In theory, running the bud twice will always be more efficient than one run using the same total amount of oil, but that doesn’t tell us how much is the right much either.
(missed part of your post: The material should come to equilibrium, so assuming you eyeball some 30%thc bud, the math says:
pot 1 = 8oz oil / 1oz bud = 9oz @ 3.3%thc per oz, so the bud still has a tenth of the original cannabinoids in it. Too much oil
pot 2 = 8oz oil / 4oz bud = 12oz @ 10%thc, so the bud still has a third of the original cannabinoids. Second run gets 4oz down to 3.3% using two cups coconut oil.
pot 3 = 8oz oil / 8oz bud = 16oz @ half of the original cannabinoids. When run a second time with a fresh 8oz oil = 7.5% Third run gets all eight ounces down to 3.75% with three cups coconut oil.