You see Dick was thirteen when the first season started so that means he's either thirteen or fourteen when the first season ended. Now Dick becoming Nightwing has always been a coming of age story so the perfect age for him to become Nightwing is around the age of 18, see the problem I'm having? Dick is 18 or barely 19 in the second season. Even if you lower the age of Dick becoming Nightwing to 17 years old there is still not enough time for two new Robins, unless you lower it even more to the age of fourteen, but that is rather ridiculous and way too young.
And yes I actually thought this one through. I wish others, especially from someone called Mr. Holmes, would do the same.