I can't think of a way of getting a singularity. As soon as the mass in a region of space becomes high enough to start a black hole, time would freeze and it would take several millions universe lifetimes for the mass to fully collapse into itself, no matter how close of far the observer is to the mass. The way I see it, things would go on as usual inside the black hole, but there's a universal curtain preventing anyone from accessing the interior.
That's not how black holes work. It takes an infinite amount of time for the light at the event horizon to escape, true. But you can think of it as if it's an "optical effect".
If you are a free-falling observer, _nothing_ changes for you locally at the event horizon. You will cross it and reach the singularity within a finite (and quite short) time.
Well, at some point space-time warps so much that unless you are at the center of the would-be singularity, you'd see everything closer to it than you freeze-out as an event horizon appears. If you are inside the event horizon then... I'm clueless about what you'd experience.
If I to guess, you'd see yourself outside an smaller event horizon (as nothing gets through one due to spacetime warping) and you's have a lot of mass very far behind you due again to space time warping so that yout local scape velocity is less than c.