Invariance of cross ratio under Möbius transformation and another problem related to cross ratio.
A nice way (and not that difficult) way to prove that a mobius transformation is cross ratio preserving is simply calculating it out.
Let $T$ be the mobius transformation $T(x) = \frac {ax +b}{cx +d}$
Then $$T(x) -T(y) = \frac {a x +b}{c x +d} -\frac {a y +b}{c y +d}= $$
$$ = \frac {(a x +b)(c y +d) - (a y +b)(c x +d) }{(c x +d)(c y + d)} = $$
$$ = \frac {ax(c y +d) +b(c y +d) - a y(c x +d) - b(c x +d)}{(c x) +d)(c y +d)} = $$
$$ = \frac { ac x y + adx +bc y + bd - ac xy -ady - bc x -bd}{(c x +d)(c y +d)} = $$
$$ = \frac { ad x +bc y - ad y - bc x }{(c x +d)(c y +d)} = $$
$$ = \frac{(ad-bc)(x - y)}{(c x + d)(c y +d)} $$
then taking the cross ratio
$$\frac {Tz_1-Tz_2 }{Tz_1-Tz_4} \frac {Tz_3-Tz_4 }{Tz_3-Tz_2} = $$
$$\frac {(Tz_1-Tz_2)(Tz_3-Tz_4) }{(Tz_1-Tz_4)(Tz_3-Tz_2)} = $$
$$ = \frac {( \frac{(ad-bc)(z_1-z_2 )}{(c z_1 + d)(c z_2 +d)})( \frac{(ad-bc)(z_3-z_4)}{(c z_3 + d)(c z_4 +d)}) }{( \frac{(ad-bc)(z_1-z_4)}{(c z_1 + d)(c z_4 +d)})( \frac{(ad-bc)(z_3-z_2)}{(c z_3 + d)(c z_2 +d)})} = $$
$$ = \frac {(z_1-z_2)(z_3-z_4) }{(z_1-z_4) (z_3-z_2)} = $$
$$=\frac {z_1-z_2 }{z_1-z_4} \frac {z_3-z_4 }{z_3-z_2} $$
where you started with.
Your proof is correct, except that you probably mean $H \circ T^{-1}(T(z_1))$.
For part (b), do you already know that the image of a line (along with $\infty$) or circle under a Moebius transformation is a line or circle?
If so, then part (b) follows from part (a) can be proved as follows. The image under $H$ of the line or circle $C$ through $z_2$, $z_3$, $z_4$ is the line or circle through 0, 1, $\infty$, which is of course $\mathbf{R} \cup \{\infty\}$. So asking whether $z_1$ is on $C$ is the same as asking whether $H(z_1)$ is in its image, which is $\mathbf{R} \cup \{\infty\}$.
If you don't know this fact, then you can analyze the argument of $(z_1, z_2, z_3, z_4)$ as being the oriented angle $\angle z_4 z_1 z_2$ minus the angle $\angle z_4 z_3 z_2$. By the inscribed angle theorem of elementary geometry, the four points $z_1$, $z_2$, $z_3$, $z_4$ are then concyclic or aligned if and only if these two angles differ by 0 modulo $\pi$, i.e., if and only if the argument of their cross ratio is 0 or $\pi$.
Edit: Your proof depends on the uniqueness of the Moebius transformation sending three given points to 0, 1 and $\infty$, but the statement seems to view this fact as already known.