Update: may have figured it out (below)
I've been reading Preskill's notes on vortices, and he's included a couple of exercises at the end of section 1.3.
In the first, you must look at the breaking of $G = SU(2)_1\times SU(2)_2 \times U(1)_Y$ down to $H = U(1)_Q$ where $U(1)_Q$ is generated by
$Q = p T_3^{(1)} + q T_3^{(2)} + r Y$,
($p, q$ and $r$ being integers with no common factor) and show that $\pi_1 (G/H) \cong \mathbb{Z}_r$. I thought I had shown this, but the next exercise made me think I'm definitely not understanding the idea.
(I argued that, for a given $r$, the curve in $G$ generated by $Q$ will have winding number $r$. A curve in $G$ is categorised homotopically by its winding number $n$, and if composed with the $Q$ curve, the resultant curve will have winding number $n+r$ (and be homotopically equivalent to any curve with that winding number). Since modding out $H$ identifies any points lying along the $Q$ curve, this means that any two curves whose difference in winding number is $r$ differ from each other only by a curve which is homotopically equivalent to the $Q$ curve, which is now just a single point. Thus the group of homotopically distinct curves is $\mathbb{Z}_r$.)
In the next question however, he asks why the standard $SU(2) \times U(1)$ GWS model does not admit stable vortex solutions. From what I read this seems to be $SU(2) \times U(1)_Y \rightarrow U(1)_{EM}$, with the unbroken generator
$Q = T_3 + \frac{1}{2} Y$.
Reading online I do see a lot of people saying the vacuum manifold of the GWS is $S^3$, which is of course simply-connected. But I don't understand why the vacuum manifold is $S^3$. What is the deciding difference with question 1? Is my previous argument nonsense?
I'm also in the market for a systematic way to calculate the vacuum manifold of a quotient group (though as you may be able to tell my mathematical level is not high enough to tackle a pure-maths approach).