This paper studies generalized Hamiltonian gradient flows for contact-type Hamilton--Jacobi equations, adopting the variational framework of Herglotz's principle and its fundamental solution hL(t,x,y,u). Two main results are presented. First, precise first-order sensitivity relations are derived, linking derivatives of hL
Nearby in the stack
to dual arcs of minimizing trajectories. Second, quantitative second-order estimates show that
hL
is locally semiconcave and, over short time, semiconvex, indeed uniformly convex in certain variables. These regularity properties follow from a detailed variational analysis of minimizing trajectories. The work establishes a foundation for intrinsic methods in analyzing singularity propagation and generalized gradient flows in contact context, with implications for weak KAM theory, optimal transport, and regularity of viscosity solutions.