Let me give an example showing that the normality hypothesis is necessary.

Let $Y=\mathbb{P}^1$ with natural $G=\mathbb{G}_m$-action. Let $X$ be the $G$-variety obtained by glueing transversally the two fixed points $0$ and $\infty$. Consider the line bundle $\mathcal{O}(l)$ with $l\neq 0$ on $Y$ and glue the fibers over $0$ and $\infty$ using any linear isomorphism to obtain a line bundle $\mathcal{L}$ on $X$. Suppose that $\mathcal{L}$ has a $G$-linearisation. Pulling it back to $Y$, we obtain a $G$-linearisation of $\mathcal{O}(l)$ on $Y$ such that $G$ acts on the fibers over $0$ and $\infty$ with the same character. However, the description of the $G$-linearisations of $\mathcal{O}(l)$ when $l\neq 0$ shows that this is not possible (more precisely, for any $G$-linearisation of $\mathcal{O}(l)$, the characters through which $G$ acts on the fibers over $0$ and $\infty$ differ by the character $t\mapsto t^l$). This argument shows moreover that no multiple of $\mathcal{L}$ has a $G$-linearisation.

Note that it follows that there is no ample $G$-linearised line bundle on $Y$.

As for the second question, the natural map to study is more likely to be $Pic^G(X)\to Pic(X)^G$ where $Pic(X)^G$ denotes the group of line bundles whose class is $G$-invariant. When $X$ is normal and proper, its Picard group is an extension of a discrete group by an abelian variety so that if $G$ is linear connected, $G$ acts necessarily trivially on $Pic(X)$ and $Pic(X)^G=Pic(X)$. However, when $X$ is not normal, this is not the case anymore (for instance in the above example).