Because N1 has already passed T2 according to N1 there was a moment in the past when the observer at N1 could look down and see the observer at T2.
In which frame? You can't mix frames. You need to specify whose "moments" (i.e. whose time) you're using. This sloppiness has been a constant characteristic of your "work" with relativity forever. How do you ever expect to understand it if you forget to pay attention to which reference frame you're using? Relativity is all about translating from one frame to another.
In your top picture, T1 is aligned with N2. T2 passed N1 some time in the past, according to the observer on
ship 1.
In your bottom picture, T1 is aligned with N2, again. N1 has yet to pass T2, according to the observer on
ship 2.
I've bolded the observers in each case, to draw your attention to the relevant frames. You even drew the pictures yourself and labelled them "Ship 1 at rest on top" and "Ship 2 at rest at bottom". That is, two pictures, one drawn from the perspective of ship 1 and one drawn from the perspective of ship 2.
So, let's correct your statements:
"Because N1 has already passed T2
according to N1 there was a moment in
the observer 1's past when the observer at N1 could look down and see the observer at T2,
according to the observer on ship 1."
And:
"Because N1 has not yet reached T2
according to the observer at T2 (i.e.
as measured by the observer on ship 2), there wasn't a moment in
the observer 2's past when the observer at T2 could look up and see the observer at N1."
What's impossible about it? You have two different observers. One sees T1 and N2 align before T2 and N1; the other sees T2 and N1 align before T1 and N2.
They do not agree that the two alignments happen in the same time order.
Get it yet?