(1) Let $X\subseteq\Bbb R$ be uncountable. For $n\in\Bbb Z^+$ let $$L_n=\left\{x\in X:\left(x-\frac1n,x\right]\cap X\text{ is countable}\right\}$$ and $$R_n=\left\{x\in X:\left[x,x+\frac1n\right)\cap X\text{ is countable}\right\}\;.$$
Fix $n\in\Bbb Z^+$. The family $\left\{\left[x,x+\frac1n\right):x\in R_n\right\}$ is an open cover of $R_n$ in the Sorgenfrey topology, which is hereditarily Lindelöf, so there is a countable $C\subseteq R_n$ such that $\left\{\left[x,x+\frac1n\right):x\in C\right\}$ covers $R_n$. But for each $x\in C$ we have $\left[x,x+\frac1n\right)\cap R_n\subseteq\left[x,x+\frac1n\right)\cap X$, a countable set, so $R_n$ is countable. The same argument using the reverse Sorgenfrey topology shows that each $L_n$ is countable. Thus,
$$\bigcup_{n\in\Bbb Z^+}(L_n\cup R_n)$$
is countable. Let $$X_0=X\setminus\bigcup_{n\in\Bbb Z^+}(L_n\cup R_n)\;;$$
you can check that for each $x\in X_0$ and each $\epsilon>0$, the sets $[x,x+\epsilon)\cap X_0$ and $(x-\epsilon,x]\cap X_0$ are not just non-empty, but actually uncountable.
(2) is false as stated. Let $\mathscr{B}$ be the set of open intervals with rational endpoints; $\mathscr{B}$ is countable, so we can enumerate it as $\mathscr{B}=\{B_n:n\in\Bbb N\}$. For each $n\in\Bbb N$ let $x_n\in B_n$ be irrational. Let $D=\{x_n:n\in\Bbb N$, and let $X=[0,1]\setminus D$; certainly $X$ is uncountable. Suppose that $[a,b]\cap X$ is an interval in $X$; without loss of generality we may assume that $0\le a<b\le 1$. Then there is an $n\in\Bbb N$ such $B_n\subseteq[a,b]$, and by construction $x_n$ is then an irrational in $[a,b]\setminus X$. Thus, $X$ contains no interval $[a,b]\setminus\Bbb Q$ of irrationals.