Since 2 and 3 were already answered by @pitariver in the comments, I'll only say something that partially answers 1.
Let's call $\mathrm{Hol}(T)$ to the image of the holomorphic functional calculus for $T$ in $B(H)$. In general $\mathrm{Hol}(T)$ is not all of $B(H)$ simply because $\mathrm{Hol}(T)$ will always be a commutative unital subalgebra of $B(H)$. Indeed, let $f, g$ be holomorphic functions in a neighborhood of $\sigma(T)$, then the function $fg=gf$ is also holomorphic and since the functional calculus is an algebra homomorphism we have
$$
f(T)g(T)=(fg)(T)=(gf)(T)=g(T)f(T)
$$
As for what exactly is the image in $B(H)$, we have to look at the Banach subalgebra of $B(H)$ generated by $T$, which is the smallest Banach subalgebra in $B(H)$ that contains $T$. Let's call it $\mathrm{Ban}(T)$, which is clearly a closed commutative subalgebra of $B(H)$.
We claim that $\mathrm{Hol}(T) \subseteq \mathrm{Ban}(T)$. To prove this, let $f$ be a holomorphic function on an open neighborhood of $\sigma(T)$, say $\Omega$. Using basic complex analysis we can write $\Omega$ as countable increasing sequence of compacts subsets and use Stone-Weierstrass to find polynomials $p_n$ such that $p_n \to f$ in the uniform convergence on compact subsets of $\Omega$. Then, by basic properties of the holomorphic functional calculus we have that $\|p_n(T)-f(T)\| \to 0$. Since each $p_n(T) \in \mathrm{Ban}(T)$, it follows that $f(T) \in \mathrm{Ban}(T)$. This proves the claim.
As far as I know this is the best result we can get. I wasn't able to quickly find a counter example to show that the inclusion $\mathrm{Hol}(T) \subseteq \mathrm{Ban}(T)$ is proper. I suspect $\mathrm{Hol}(T)$ might not even be closed in $\mathrm{Ban}(T)$ but I also don't have an example for this.