The currently accepted answer sidesteps the question about calculating what events can actually be seen using Schwarzschild coordinates. It is possible to find an answer to this question using Schwarzschild coordinates, both numerically and analytically. The answer of course is that the past light cone for the limiting case does not encompass the entire universe outside the black hole and that there is a finite time available to signal to a falling object (even in Schwarzschild coordinates), that depends on where the falling observer was released from.
There are two separate problems, each with two separate cases. The first is to work out whether light intercepts a falling observer before they reach the event horizon. However there is then a small additional correction to be made to work out whether a light signal can still intercept a falling observer after they cross the event horizon but before they reach the singularity.
1. Whether light can intercept an object before it reaches the event horizon
(a) Object falling from infinity
I start off with an observer at a radius $r_0$ (all radii are expressed as multiples of the Schwarzschild radius $r_s$). The observer is passed at time $t_0$ (in Schwarzschild coordinates, which is equal to $\tau =0$ according to the observer's own clock), by an object falling radially inward towards the black hole from infinity (where it started at rest). At some time $\Delta t$ later, the observer fires a laser beam radially inwards. The problem is to work out the maximum $\Delta t$ that will intercept the falling object and then convert this to a $\Delta \tau$ in terms of proper time according to the observer. That there must be a maximum $\Delta t$ and $\Delta \tau$ is conceptually easily established by considering (e.g.) Kruskal-Szekeres coordinates.
The null geodesic (in Schwarzschild coordinates) that the inwardly travelling light follows (in $c=1$ units) is:
$$ t = -r - r_s \ln \left| \frac{r -r_s}{r_0-r_s}\right| + a + \Delta t\, ,\tag{1}$$
where the constant $a = r_0 + t_0$.
The geodesic followed by a body released at rest from infinity is (e.g. see eq. 25.38 in the "Orbits of Particles" section of "Gravitation" by Misner, Thorne & Wheeler, 2017, Princeton University press)
$$t = r_s \left( -\frac{2}{3}\left(\frac{r}{r_s}\right)^{3/2} - 2\left(\frac{r}{r_s}\right)^{1/2} + \ln \left| \frac{\sqrt{r/r_s} + 1}{\sqrt{r/r_s} -1}\right|\right) + b \tag{2}$$
The constant $b$ can be chosen to ensure that the object passes through the point $(t_0, r_0)$ - thus:
$$b = t_0 - r_s\left( -\frac{2}{3}\left(\frac{r_0}{r_s}\right)^{3/2} - 2\left(\frac{r_0}{r_s}\right)^{1/2} + \ln \left| \frac{\sqrt{r_0/r_s} + 1}{\sqrt{r_0/r_s} -1}\right|\right) \tag{3}$$
By plotting these geodesics and using a bisection method to determine when and if they intersect, I was able to determine the maximum $\Delta t$
($T$ in the OP, although I started my object in freefall from infinity) that still permits the light to intercept the falling object as a function of where that light is emitted from. The result appears stable to reducing the tolerance (I used $10^{-14}r_s$).
An example of the limiting case is shown below. The red curve is the light geodesic whilst the blue curve shows the geodesic of an object falling from infinity and passing through (in this case) $5.8r_s$ at $t=0$. Only events below the red curve could be seen by a falling observer.
I then "derived" this curve analytically. Rearranging equation (1) we can write
$$ r - r_s = (r_0-r_s) \exp((a + \Delta t -r)/r_s) \exp(-t/r_s) $$
and if (close to the limit where it is possible for light to intercept the falling object) we let $t$ become large, then $r \rightarrow r_s$ and we can write
$$ r - r_s \simeq (r_0 - r_s) \exp((a + \Delta t -r_s)/r_s) \exp(-t/r_s) \, , \tag{4}$$
where we exploit that fact that the limit of $r \exp(-r/r_s)$ as $r\rightarrow r_s$ is just $r/e$.
Rearranging equation (2) in a similar way, we get
$$\frac{\sqrt{r/r_s} - 1}{\sqrt{r/r_s} +1} = \exp(-t/r_s)\exp\left(-\frac{2}{3}\left(\frac{r}{r_s}\right)^{3/2} -2\left(\frac{r}{r_s}\right)^{1/2} + \frac{b}{r_s} \right)\, . $$
Again, we argue that around the limiting case $r \rightarrow r_s$ and so we can write
$$ \sqrt{r/r_s} = 1 + 2\exp(b/r_s - 8/3)\exp(-t/r_s)$$
Squaring this and neglecting the $\exp(-2t/r_s)$ term:
$$ r - r_s \simeq 4r_s \exp(b/r_s - 8/3)\exp(-t/r_s)) \tag{5}$$
Whether there is an interception point or not is determined by whether the ratio of equations (4) and (5) is less than 1 as $t \rightarrow \infty$.
$$\lim_{t\rightarrow \infty} \frac{(r_0 - r_s) \exp((a + \Delta t -r_s)/r_s) \exp(-t/r_s)}{r_s( 1 + 4\exp(b/r_s - 8/3)\exp(-t/r_s))} < 1\,$$
which leads to
$$\frac{(r_0 - r_s) \exp((a + \Delta t -r_s)/r_s)}{4r_s \exp(b/r_s - 8/3)} < 1$$
$$ \exp(\Delta t/r_s) < \frac{4r_s}{r_0 - r_s} \exp(\frac{b - a}{r_s} - \frac{5}{3}) $$
$$ \Delta t < \ln \left(\frac{4r_s}{r_0 - r_s}\right)r_s + \left(\frac{b - a}{r_s} - \frac{5}{3}\right)r_s$$
Reinserting the expressions for $a$ and $b$
$$\Delta t < \ln \left(\frac{4r_s}{r_0 - r_s}\right)r_s + \left( \frac{2}{3}\left(\frac{r_0}{r_s}\right)^{3/2} + 2\left(\frac{r_0}{r_s}\right)^{1/2} - \ln \left| \frac{\sqrt{r_0/r_s} + 1}{\sqrt{r_0/r_s} -1}\right| - \frac{5}{3}\right)r_s - r_0$$
This matches what is plotted above.
To turn this into a maximum proper time interval $\Delta \tau$ from the point of view of the observer, the result would be multiplied by $(1 - r_s/r_0)^{1/2}$.
(b) Object falling from rest at $t_0, r_0$
Now the setup is that the observer releases the object from $t_0, r_0$, then waits a (coordinate) time interval $\Delta t$ before signalling.
Equation (1) is still valid in this scenario, however equation (2) needs to be replaced by the following geodesic for an object freely falling from rest at $t_0, r_0$.
$$ \frac{t-t_0}{r_s} = \ln \left| \frac{ (r_0/r_s -1)^{1/2} + \tan (\eta/2)}{(r_0/r_s -1)^{1/2} -\tan(\eta/2)}\right| + \left(\frac{r_0}{r_s}-1\right)^{1/2} \left( \eta + \frac{r_0}{2r_s}(\eta + \sin \eta)\right). \tag{6}$$
Here the "cycloid parameter" $\eta(r)$ is defined by
$$r = \frac{r_0}{2}(1 + \cos \eta)$$
As $r \rightarrow r_s$, the first term in equation (6) grows exponentially whilst the second term, which I will define as $b(r)/r_s$, tends to a constant:
$$ \lim_{r \rightarrow r_s} b(r) = b_{\rm rs} = r_s\left(\frac{r_0}{r_s}-1\right)^{1/2} \left( \eta_{\rm rs} + \frac{r_0}{2r_s}(\eta_{\rm rs} + \sin \eta_{\rm rs})\right), $$
where
$$\cos \eta_{\rm rs} = \left(\frac{2r_s}{r_0} -1 \right).$$
Using the identity that $\tan \eta/2 = \sin \eta/(1 + \cos \eta)$, then
$$\tan (\eta/2) = \left( \frac{r_0}{r} - 1 \right)^{1/2}.$$
Substituting this into equation (6) we can set $t_0=0$, exponentiate and find
$$\left(\frac{r_0}{r_s}-1\right)^{1/2}\left(1 - \exp\left[\frac{b-t}{r_s}\right]\right) = \left(\frac{r_0}{r}-1\right)^{1/2} \left( 1 + \exp\left[\frac{b-t}{r_s}\right]\right)$$
Squaring this and neglecting terms containing $\exp(-2t/r_s)$ as $t$ becomes large, this can be rearranged to give
$$ r = r_s\frac{\left(1 + 2\exp[(b-t)/r_s]\right)}{1 - 2\exp[(b-t)/r_s] + (4r_s/r_0)\exp[(b-t)/r_s]}.$$
Again, as we are looking for a limiting behaviour at large $t$, then the denominator can be expanded as a binomial, retaining only the first two terms. Multiplication with the numerator then yields:
$$ r -r_s \simeq 4r_s \left(1 - \frac{r_s}{r_0}\right) \exp\left[\frac{b-t}{r_s}\right]. \tag{7}$$
To find the limiting $\Delta t$ for which a light beam from the observer will "catch" the falling object, we take the ratio of equations 4 and 7, set $b=b_{\rm rs}$ and demand that this is less than 1. This yields
$$ \exp\left[\frac{\Delta t}{r_s}\right] < 4 \left(\frac{r_s}{r_0}\right) \exp\left[\frac{b_{\rm rs}}{r_s}\right] \exp\left[\frac{r_s-r_0}{r_s}\right]$$
and hence
$$\Delta t < r_s \ln \left(\frac{4r_s}{r_0}\right) + b_{\rm rs} + r_s - r_0$$
The result is plotted below as the red curve (and I have confirmed that it is correct using a numerical bisection method) and compared to case 1 with the free falling object from infinity (blue curve, as in the first picture). As expected the allowed $\Delta t$ is larger when the object is released from rest.
As before, this result is the maximum Schwarzschild coordinate time interval. It must be reduced by the appropriate time-dilation factor $(1-r_s/r_0)^{1/2}$ to yield the maximum proper time interval.
An example of the limiting case is shown below. The red curve is the geodesic of light, the blue curve is the geodesic of the falling object. Only events below the red curve (which asymptotes to a gradient of -1) can be "seen" by an object falling into a black hole from rest, from (in this case) about $5.8r_s$.
2. Whether light can intercept an object before it reaches the singularity
The answer above give the maximum (coordinate) time-delay for a signal from a stationary observer to reach a falling object before it reaches the event horizon, $(\Delta t)_{\rm EH}$. But that does not completely answer the (headline) question, because the object can still receive light during the time it takes to reach the singularity after crossing the event horizon. This is most clearly seen in Kruskal-Szekeres coordinates, but again it is possible to solve this (rather easily) in Schwarzschild coordinates.
The condition here is that the coordinate time of the delayed light geodesic must be less or equal to the coordinate time of the falling object geodesic at $r=0$.
This condition is actually rather easy to find. For the case of the object free-falling from infinity, equations (1-3) show that the original $\Delta t$ that I derived should be increased as
$$(\Delta t)_{\rm singularity} = r_s \ln \left( \frac{r_s}{r_0-r_s}\right) - r_s\left( -\frac{2}{3}\left(\frac{r_0}{r_s}\right)^{3/2} - 2\left(\frac{r_0}{r_s}\right)^{1/2} + \ln \left| \frac{\sqrt{r_0/r_s} + 1}{\sqrt{r_0/r_s} -1}\right|\right) - r_0$$
Or in terms of the previous result.
$$ (\Delta t)_{\rm singularity} = (\Delta t)_{\rm EH} +r_s\left(\frac{5}{3} - 2\ln 2\right) =(\Delta t)_{\rm EH} + 0.280r_s $$
For the case of an object falling from rest, we see that $\eta = \pi$ at $r=0$, so that if the coordinate time to be less or equal to the coordinate time of the object at $r=0$ is obtained from equations (1) and (6) as
$$ (\Delta t)_{\rm singularity} = r_s \ln \left(\frac{r_s}{r_0-r_s}\right) + \pi r_s\left(\frac{r_0}{r_s} -1\right)^{1/2}\left(1 + \frac{r_0}{2r_s}\right) -r_0,$$
which is larger than $(\Delta t)_{\rm EH}$ by an amount that depends on $r_0$, but is asymptotic to the falling from infinity results as $r_0$ becomes large.
This new relationship is plotted below - the higher red curve is the maximum (coordinate time) delay that can be tolerated and still send a signal that reaches the falling object before the singularity. The lower plot shows the difference between this and the previous result for the delay to still reach the object before the event horizon.
The plot below should make things clearer. It shows the geodesics either side or $r_s$ in the case of an object falling from $r=2r_s$ at $t=0$. The light geodesic in red is the one calculated so that it just intercepts the object as $r \rightarrow r_{s}$ and has $(\Delta t)_{\rm EH} = 3.834 r_s/c$. But we see that this geodesic "overtakes" the falling object before it reaches the singularity at $r=0$. However, the green light geodesic, with $(\Delta t)_{\rm singularity} = 4.283 r_s/c$ intercepts the object geodesic at exactly $r=0$.