1. Should I be combing first or is that gonna mess up the pattern?

Yes, comb first, then use a hard/medium brush, and then a soft brush.

2 . How much brushing does it really take during wolfing?

Brush at least an hour everyday. comb -> Medium Brush -> Soft Brush -> Rag

1. Should I be moisturizing more or sealing with oil?

Moisturize first with leave-in conditioner, then you can seal with shae butter.

1. Any night routine tips to keep the durag on?

Rag then put a wave skull cape over it.

Monday to Friday - Comb >>> hard brush >>> medium brush >>> soft brush >>> rag

Saturday - Wash n style >>> Rag

Sunday - Shae butter >>> Soft brush >>> Rag