I push my cuticles back when I am in the shower. Seems to be easier and less damaging.
Olive oil is awesome for the cuticles.
File in the same direction each time.
Don't use polish that has formaldehyde in it.
Don't soak your nails. Short times like 5 mins is ok.
Turn around time to good nails and cuticles takes work. Once you get them nice it will much easier to keep them up.
The cuticles will heal faster than your nails.
I've found that almost any cream can work you just need to use it often.
I use Philosphy's save the nails on my husbands awful cuticles and it worked just as good as a Sally Hansen cream I got. Only I had to apply it everynight before bed after he washed his hands.