Contexts (it must also be noted that as $\delta t$ tends to zero, $\delta \theta$ also tends to zero):
First context $$ \lim_{\delta t \to 0} \frac{-2v\sin(\delta\theta/2)^2}{\delta t} = \lim_{\delta t \to 0} \frac{-2v(\delta\theta/2)^2}{\delta t}\quad\text{[since $\sin(x) \to x$ as $x \to 0$]} $$ Second context $$ \lim_{\delta t \to 0} \frac{v\sin(\delta\theta) - 0}{\delta t} = \lim_{\delta t \to 0} \frac{v\sin(\delta\theta)}{\delta t} = \lim_{\delta t \to 0} \frac{v\delta\theta}{\delta t} = v\omega = r\omega^2\quad\text{[since $\sin(x) \to x$ as $x \to 0$]} $$ The only reason that I am given is that as $x$ tends to zero, $\sin x$ tends to $x$, which for one does not only not make sense, but also doesn't help to clarify why $(\sin x)^2=x^2$ in the first context. So, I was wondering if someone could either provide me with the correct explanations or explain the ones provided.
As @NoahSchweber pointed out, strictly speaking, $\sin(x) \to x$ is nonsense; what it means is that $\sin(x)/x \to 1$. This indicates that, with care (see @Bernard's post for details), you may replace $\sin(x)$ by $x$ in limits. Assuming that $\Delta\theta \to 0$ as $\Delta t \to 0$ (EDIT: as I see that you said is the case), you have, for example, $$ \lim_{\Delta t \to 0} \frac{-2v\sin^2(\Delta\theta/2)}{\Delta t} = \lim_{\Delta t \to 0} \Bigl(\frac{\sin(\Delta\theta/2)}{\Delta\theta/2}\Bigr)^2\cdot\frac{-2v(\Delta\theta/2)^2}{\Delta t} = \lim_{\Delta t \to 0} \frac{-2v(\Delta\theta/2)^2}{\Delta t}, $$ as long as the last limit exists, which it need not without an additional hypothesis (namely, the differentiability of $(\Delta\theta)^2$ as a function of $\Delta t$ at $\Delta t = 0$).