Take a simple random walk $\gamma$ in the complex plane conditioned to start at point $a$ and end at point $b$. For this random walk, we can define the winding number $W_\gamma(a,b)$ around $b$ in the usual way for complex curves.
If instead we have a 2D Brownian motion $Z=X+iY$, then this definition becomes more complicated. For example, if we have a Brownian motion starting at the origin, we can talk about the winding number $\theta_t$ at time $t$ around the origin by solving the stochastic differential equation
with initial condition $\theta_0=0$.
The issue is that for Brownian motion, we cannot condition on the path $Z$ to hit a particular point, because this has probability zero. Moreover, by considering annuli around $b$ and the fact that planar Brownian motion moves between concentric annuli with positive probability, it seems to me the situation becomes rather singular.
Question: Is there a sensible generalization for the winding number of a Brownian motion conditioned to hit a single point?
For example, can we look at the limit of the winding number around an annulus about point $b$ whose radius shrinks to zero? I would imagine we would require the Brownian motion to be conditioned to hit some region of positive area just outside the shrinking annulus.