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December 7th, my two year two, beautiful grey cat gave birth to five kittens. Two of which got sick, one dying.
They all switched to dry hard cat food.

April 3rd, the same mom, grey, gave birth to eight kittens. A total of four were dead when they came out, three dying later one in their own ways.

The one still living, Rocket, acts weird, she sleeps away from it. We still have two cats from her first litter, one named Skeeter. Well, recently Skeeter has been drinking her milk again, is this harmful in anyway? What should I do?

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This will not do the older kitten any harm, but it won't be helping the mother to provide milk for the younger kitten and in fact will, most likely, do the younger kitten harm, as there's clearly health problems to have so many kittens dying.

You should be concerned with the kittens that are sick and dying, and the mother's health. Take the small, struggling kitten and the mother to the vet asap.

Keep the older kitten away from the mother, she needs all her strength for the sick smaller kitten. That milk is specialised for the needs of the younger kitten and not for a five month old kitten.

Also, get all your cats desexed.

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    I'd suggest getting to the vet to have the mother checked ASAP, and as soon as humanely possible have all the cats neutered. The current situation is just a little neglect or bad luck away from an uncontrolled indoor/outdoor colony of extremely sick cats.
    – Stig Tore
    Apr 23 '18 at 13:51
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    @StigTore yes you make valid points, I should add in the vet - it was implied in the sentence "You should be concerned with the kittens that are sick and dying, and the mother's health", but it is better to be explicit. Thanks for that
    – user6796
    Apr 23 '18 at 18:08

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