I usually stretch for 3-4 months, I have stretched up to 7 months before. What I find works best (after a lot of trial and error) is co-washing twice a week (I use a cleansing moisturizing conditioner), rollersetting, and massaging NG with jojoba oil twice a day. I never comb my dry hair with anything other than my fingers. Also, before I cleanse my hair I apply oil and finger comb to remove any shedded hair that may be stuck in the NG.
I wear updo's must of the time with the help of claw clips, banana clips and hair pins.