[proofplan]
We prove both assertions directly from the two-point definition of convexity. For the image statement, two points of $T(C)$ are represented as images of two points of $C$, and affinity of $T$ moves the convex combination through $T$. For the preimage statement, two points of $T^{-1}(D)$ have images in $D$, and affinity shows that the image of their convex combination is a convex combination in $D$.
[/proofplan]
[step:Use affinity to move convex combinations through $T$]
Since $T: V \to W$ is affine, for every $x_0, x_1 \in V$ and every $t \in [0,1]$,
\begin{align*}
T((1-t)x_0 + t x_1) = (1-t)T(x_0) + tT(x_1).
\end{align*}
This is the only property of affine maps used below.
[/step]
[step:Represent two points of the image by points of $C$]
Assume $C \subset V$ is convex. To prove that $T(C)$ is convex, let $y_0, y_1 \in T(C)$ and let $t \in [0,1]$. By the definition of image, there exist $x_0, x_1 \in C$ such that
\begin{align*}
y_0 = T(x_0)
\end{align*}
and
\begin{align*}
y_1 = T(x_1).
\end{align*}
Since $C$ is convex and $x_0, x_1 \in C$, the point
\begin{align*}
x_t := (1-t)x_0 + t x_1
\end{align*}
belongs to $C$.
[/step]
[step:Conclude that the image is convex]
Using affinity of $T$ at the points $x_0,x_1 \in V$, we compute
\begin{align*}
(1-t)y_0 + t y_1 = (1-t)T(x_0) + tT(x_1).
\end{align*}
Therefore
\begin{align*}
(1-t)y_0 + t y_1 = T((1-t)x_0 + t x_1).
\end{align*}
By the definition of $x_t$, this gives
\begin{align*}
(1-t)y_0 + t y_1 = T(x_t).
\end{align*}
Since $x_t \in C$, we have $T(x_t) \in T(C)$. Hence
\begin{align*}
(1-t)y_0 + t y_1 \in T(C).
\end{align*}
Because $y_0,y_1 \in T(C)$ and $t \in [0,1]$ were arbitrary, $T(C)$ is convex.
[/step]
[step:Pull the convexity test back through $T$]
Assume $D \subset W$ is convex. To prove that $T^{-1}(D)$ is convex, let $x_0,x_1 \in T^{-1}(D)$ and let $t \in [0,1]$. Define
\begin{align*}
x_t := (1-t)x_0 + t x_1.
\end{align*}
By the definition of preimage, $T(x_0) \in D$ and $T(x_1) \in D$. Since $D$ is convex, the point
\begin{align*}
(1-t)T(x_0) + tT(x_1)
\end{align*}
belongs to $D$.
[guided]
We want to prove that $T^{-1}(D)$ is convex, so we must start with two arbitrary points of $T^{-1}(D)$ and show that their convex combinations remain in $T^{-1}(D)$. Let $x_0,x_1 \in T^{-1}(D)$ and let $t \in [0,1]$. Define
\begin{align*}
x_t := (1-t)x_0 + t x_1.
\end{align*}
The target conclusion is $x_t \in T^{-1}(D)$, which by definition means $T(x_t) \in D$.
Because $x_0,x_1 \in T^{-1}(D)$, their images satisfy $T(x_0) \in D$ and $T(x_1) \in D$. Now we use convexity of $D$: since $D$ contains both $T(x_0)$ and $T(x_1)$, it also contains their convex combination
\begin{align*}
(1-t)T(x_0) + tT(x_1).
\end{align*}
The reason affinity is relevant is that this convex combination in $W$ is exactly the image under $T$ of the convex combination in $V$.
[/guided]
[/step]
[step:Conclude that the preimage is convex]
By affinity of $T$,
\begin{align*}
T(x_t) = T((1-t)x_0 + t x_1).
\end{align*}
Therefore
\begin{align*}
T(x_t) = (1-t)T(x_0) + tT(x_1).
\end{align*}
The right-hand side belongs to $D$, so $T(x_t) \in D$. By the definition of preimage, $x_t \in T^{-1}(D)$. Since $x_0,x_1 \in T^{-1}(D)$ and $t \in [0,1]$ were arbitrary, $T^{-1}(D)$ is convex. This proves both assertions.
[/step]