How do two H gates act on two entangled qubits?

Probably the best way to play and learn about the effect of specific gates on a state is with Quirk.

Here is the first situation you are describing (the $H$s and $CZ$):

You can hover over the amplitude graph to see the amplitude value for $|11rangle$: $-0.5$ as you correctly have.

Add the second layer of $H$s to see its effect (here):

Not change! Your math is correct (and the intuition is not, as almost always when dealing with quantum computing :) )

The reason to add that layer in Grover is because the initialization, oracle, and diffuser are different stages that are meant to be generic. They situation you are described happens specifically with this oracle, but you could change the oracle and Grover will continue working.

The compilation process takes care of these redundancies and cancel them out. Here is your example on Qiskit:

from qiskit import *
circuit = QuantumCircuit(2)
# Initialization 
circuit.h([0, 1])
# oracle
circuit.cz(0, 1)
# diffuser
circuit.h([0, 1])
circuit.z([0, 1])
circuit.cz(0, 1)
circuit.h([0, 1])

print(circuit)

     ┌───┐   ┌───┐┌───┐   ┌───┐
q_0: ┤ H ├─■─┤ H ├┤ Z ├─■─┤ H ├
     ├───┤ │ ├───┤├───┤ │ ├───┤
q_1: ┤ H ├─■─┤ H ├┤ Z ├─■─┤ H ├
     └───┘   └───┘└───┘   └───┘

Before running, the circuit is optimized in a process that Qiskit calls "transpilation":

optimized_circuit = transpile(circuit, basis_gates=['cx', 'u3'], optimization_level=3)
print(optimized_circuit)

     ┌─────────────┐     ┌─────────────┐      ┌─────────────┐
q_0: ┤ U3(π/2,0,π) ├──■──┤ U3(π/2,π,π) ├───■──┤ U3(π/2,0,π) ├
     └─────────────┘┌─┴─┐├─────────────┴┐┌─┴─┐└─────────────┘
q_1: ───────────────┤ X ├┤ U3(π/2,0,2π) ├┤ X ├───────────────
                    └───┘└──────────────┘└───┘               

This final circuit is equivalent to yours and it is closer to the circuit that will run. However, presenting you this circuit as part of the Grover explanation is not very pedagogic, as it is important to first understand each stage.