The title says "Derivatives of contravariant and covariant vectors," which would be stuff like [itex]\nabla_a v_b[/itex] versus [itex]\nabla_a v^b[/itex]. But #1 seems to be talking about [itex]\nabla_a v_b[/itex] versus [itex]\nabla^a v_b[/itex] , and #2 seems to be talking about the gradient of a scalar, [itex]\nabla_a\phi[/itex] versus [itex]\nabla^a\phi[/itex]. Which are we really talking about here?
Not to be too pedantic, but we also don't have contravariant coordinates and covariant coordinates. Coordinates are always upper-index, and an ntuple of coordinates is not a vector or covector (at least not in GR). An infinitesimal *change* in the coordinates is an upper-index vector.
Assuming that the question is really the one posed in #1, then an easy way to see this is in terms of scaling. For example, suppose you change your units from meters to centimeters. All of your coordinates (which are upper-index quantities) get bigger by a factor of 100. Now suppose you have a scalar such as the electrical potential, and you take a gradient in order to find the electric field. The electric field is *smaller* in units of V/cm than it is in units of V/m. So the coordinates transform in one way under scaling, while a gradient transforms in the opposite way. This is what we expect for covariant quantities compared to contravariant ones.