I think I've got this figured out but wanted to make sure I'm doing this right.
Working with operators that satisfy bosonic commutation relations $[b,b^\dagger] = 1$, I define a very general unitary transformation on them:
$$\gamma^\dagger = ub^\dagger + vb + w$$ where the coefficients $u$, $v$, and $w$ are real. My goal is to find the unitary operator $U$ written in the form $e^S$ where $S$ is anti-Hermitian, so that $\gamma^\dagger = e^S b^\dagger e^{-S}$.
Here's my attempt at this: The constant $w$ is straightforward using the expansion of $e^{S} A e^{-S}$ in terms of the commutator, i.e. $$e^{S} A e^{-S} = A + [S,A] + \frac{1}{2}[S,[S,A]] + \dots $$ and we see immediately that setting $S = w(b-b^\dagger)$ satisfies this. The more interesting part comes next:
The requirement that the transformation is unitary is equivalent to demanding that $[\gamma, \gamma^\dagger] = 1$ as well. This leads to the requirement $u^2 - v^2 = 1$, which in turn means that we could write these coefficients as $$u = \cosh(x), \quad v = \sinh(x)$$ for some parameter $x$. The infinitesimal transformation, $x = \epsilon \ll 1$, would then read, up to first order in $\epsilon$: $$\gamma^\dagger = b^\dagger + \epsilon b$$ Comparing this with the commutator-expansion above, we now just need to find an anti-Hermitian operator whose commutator with $b^\dagger$ is $b$. We don't even worry about the higher orders of the expansion since those are second order in $\epsilon$, but here they even vanish exactly: We simply set $$S = \frac{\epsilon}{2}(b^2 - (b^\dagger)^2)$$ since the commutator $[b^2, b^\dagger] = 2b$, and $[b,b]=0$.
I think then that I'm done: For the full transformation, I just set $$S = w(b-b^\dagger) + \frac{x}{2}\left(b^2 - b^{\dagger, 2}\right), \quad \cosh(x) = u$$
This should be true if it's true that in order to reach "angle" $x$ with our "rotation", we just have to rotate $N$ times with "angle" $x/N$, and hence in the limit $N \rightarrow \infty$ we can use the infinitesimal generator.
I know this argument works for rotations in space, where instead of $\cosh$ and $\sinh$ we'd be working with $\cos$ and $\sin$, but I'm sure this also works for the hyperbolical functions.
EDIT: The final question, now, is: Is the above reasoning sound?