kth finite difference always positive when kth derivative is?

Yes, this is true. For the function $\Delta(f,h)$ its $(k-1)$-st derivative is strictly positive, since by Lagrange theorem it equals $$f^{(k-1)}(x+h)-f^{(k-1)}(x)=hf^{(k)}(x+\theta h)>0,$$ for some $\theta\in (0,1)$. Then induct on $k$.