Here's a self-contained answer to #1.
First note/recall that any union of half-open intervals of the form $[a, b)$ is Borel. To see this, suppose that we have such a collection $[a_{x}, b_{x})$ for $x$ in some index set $X$. The set $U = \bigcup_{x\in X}(a_{x}, b_{x})$ is open, so it suffices to see that the set $Y = \{ a_{x} : x \in X\} \setminus U$ is countable.
To see that $Y$ is countable, note that we can pick for each $a \in Y$ a rational number $q_{a}$ which is in $(a_{x}, b_{x})$ for some $x \in X$ with $a_{x} = a$. Then if $x, y$ in $X$ are such that $a_{x}, a_{y}$ are in $Y$ with $a_{x} < a_{y}$, $q_{a_{x}} < b_{x}$ and $q_{a_{y}} < b_{y}$, it must be that $b_{x} \leq a_{y}$, which means that $q_{a_x} < b_{x} \leq a_{y} < q_{a_y}$.
It follows that that any union of half-open intervals is Borel.
Now let $B \subseteq \mathbb{R}$ be Borel and let $f \colon B \to \mathbb{R}$ be an increasing function. Let $E$ be the set of $x \in \mathbb{R}$ for which the set $\{ y \in B : f(y) \leq x\}$ is nonempty and bounded above. If $B$ is bounded above then $E$ is the union of all intervals of the form $[f(y), \infty)$ for $y \in B$. Otherwise, $E$ is the union of all intervals of the form $[f(y), f(z))$ for all $y \leq z$, both in $B$. Either way, $E$ is Borel.
Define $g$ on $E$ by letting $g(x) = \sup\{ y\in B : f(y) \leq x\}$. Then $g$ is an increasing function with Borel domain, so Borel, so $g^{-1}[B]$ is Borel.
To see that $f[B]$ is Borel, it suffices to see that $g^{-1}[B] \setminus f[B]$ and $f[B] \setminus g^{-1}[B]$ are both Borel.
To see the former, suppose that $x$ is in $g^{-1}[B] \setminus f[B]$. Then there exists a $z \in B$ such that $\sup\{ y\in B : f(y) \leq x\} = z$, but
$f(z) \neq x$. If $f(z) < x$, then everything in the interval $(f(z), x]$ is in $g^{-1}[B] \setminus f[B]$. If $f(z) > x$, then everything in the interval $[x, f(z))$ is in $g^{-1}[B] \setminus f[B]$. This shows that $g^{-1}[B] \setminus f[B]$ is a union of half-open intervals.
To see the latter, we show that $f[B] \setminus g^{-1}[B]$ is countable. If $x \in f[B] \setminus g^{-1}[B]$, then there is a $z \in B$ such that $f(z) = x$, but $g(x) \neq z$, which means that there is a $w > z$ in $B$ such that $f(w) = x$. So the members of $f[B] \setminus g^{-1}[B]$ induce a collection of pairwise disjoint nonempty open intervals $(z, w)$, which means that there are only countably many of them.