This is a subtle question, because what you see depends on competing effects. The answer depends on exactly how you fall into the black hole, since the appearence of objects depends very strongly on your boost. If you boost away from any object, the object will redshift, spread out in your field of vision, and dim, and if you boost toward it it will blueshift, compress into your forward field of vision and brighten. This means that what you see depends on whether you speed up toward the black hole to crash in fast, or whether you accelerate away from the black hole so that you are highly boosted outward when you cross (the typical situation for a late-falling observer)
The light-rays at the moment of crossing the horizon from the star stay on the horizon forever, so you can always (classically) collect some radiation from the star no matter how late you cross. But the image size, shape brightness and reshift depends on your boost in such a way that you never see too much of the star at late times. If you go in moving very fast toward the center of the black hole, you see a small bright image of the star directly ahead, toward the direction of the singularity whose size is inversely proportional to the time at which you cross (the affine parameter of your crossing location). If you go in naturally, meaning you spend a while accelerating near the horizon to keep from falling in, and then let yourself go, then you see a spread out dim redshifted image (the same image as before in a different frame), which is redshifted to oblivion if you come in at late times after spending much time near the horizon.
Near Horizon Solution
The near horizon form of the Schwartschild solution can be found by writing $r=2M+u^2$ in the usual r coordinate, as described here: Why is spacetime near a quantum black hole approximately AdS? . You get (choosing units so that 2M=1, and calling the Schwartschild time $\theta$):
$$ ds^2 = - u^2 d\theta^2 + du^2 + (1 + {u^2\over 4} ) d\Omega^2 $$
This is a Rindler space cross a sphere, so that you can transform it into Minkowksi space cross $S_2$ by using the coordinates $t=u \sinh(\theta)$ $x=u \cosh(\theta)$
$$ ds^2 = - dt^2 + dx^2 + (1 + {x^2 - t^2\over 4} ) d\Omega^2 $$
This is the near horizon form, including the leading order variation in the sphere radius with distance from the horizon. The horizon is the light path $x=t$. The region $t>x$ inside the forward lightcone of the origin is the region in which the sphere radius contracts, and this is the interior of the black hole, while the region $t<x$ spacelike and to the right of the origin is the exterior of the black hole
The problem is ray-tracing in a Schwarzschild geometry, so one has to consider light rays starting at a crossing point $x=t=t_0$ on the horizon. The backward light cone from this point can be parametrized by choosing a past-pointing vector in M_2, and adding the appropriate length component along the sphere.
No winding
The main issue in the solution of the problem is whether you see multiple images. The light rays near the horizon going close to outward slowly travel around the black hole surface, and you might thing that you can see many images of the star, due to rays that slowly crawl around the black hole to reach you from the star after a winding.
This is not so, because the time for one winding is always comparable to the time it takes the light to get away from the surface of the black hole. This is easiest to see in the product near-horizon solution.
Given a light ray coming into your eya at small angle $\theta$ from directly toward the center of the black hole, the failure of the ray to be the horizon generator is proportional to $\theta^2$, while the component along the sphere factor of the near horizon solution is proportional to $\theta$.
But if you look at the quantity $x^2-t^2$, which is $u^2$,the squared difference of the radial Schwarzschild coordinate from 2M, along the approximate geodesic, it is
$$ (t-s)^2 - (t - s\cos(\theta))^2 = s(t-s)\theta^2 $$
This quantity increases to a maximum of $(t\theta/2)^2$. When this maximum is comparable to 1, the light ray traced back escapes from the gravitational product region. This heuristic shows that the escape time is for $\theta\propto 1/t$, up to small factors of order unity.
Since the winding time is also $t\propto 1/\theta$, there are no windings--- the light ray escapes the near-horizon product region before it can go once around.
Size of the stellar image
The angular size of the stellar image is determined by the affine-parameter to escape the horizon region for a back-traced ray at angle $\theta$ away from the line toward the center of the black hole.
Since the solution looks (nearly) like a product right by the horizon, the geodesics are simply straight lines in the Minkowski space, which simultaneously wind around the sphere. No-winding shows that the angular spread of the image of the star (assuming you come in in the same boost frame as the star when the star crosses the horizon) is less than the angle which will wind one full turn in the affine parameter $t$ where you cross.
This means that the angular spread of the star falls as $1/t$. This is the image in the unboosted frame, which is defined by translating the frame of the infalling star with no boosting in the Minkowksi space factor of the product
Boosting effects
The effect of boosting is a conformal transformation of the sphere of incoming light rays. This is described very nicely in Penrose's Spinors and Space-Time Vol.1. The qualitative effect is clear--- if you go very fast in a certain direction, light in your frame has additional momentum in the opposite direction, concentrating the light into your forward field of vision and blueshifting it. Light behind you is redshifted and spread into oblivion.
For a black hole, time translation along the horizon is a boost, since the external time parameter $\theta$ is a boost parameter. This means that if you wait a long time in the external coordinates, and look at the same velocity translated into the future using the time Killing vector, this velocity has been boosted away from the black hole center by an amount proprotional to the time.
The visual image of the star is only undimmed and shrunk by an amount proportional to t in the "rest frame" of the collapsing star (I put rest frame in quotes because it is a reference frame of the near horizon M_2 x S_2 metric). It is undimmed because the product nature of the solution does not let the light rays spread out, but it is shrunk to an angular size of 1/t because most of the rays miss the star.
But when you are falling in with the same velocity at late times, t, you are boosting by an amount proportional to t. A boost by an amount proprtional to t will spread the angular region behind by an exponentially growing amount in t. This leads the image to dim exponentially, so that you really won't see anything at all if you fall in at late times in a natural way.