Natural dreadlocks, from day 0
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To be honest everyone's different so I don't think there is really a rule for all but keeping on top of separating is definitely a good thing to be doing.
I only have hair on the top of my head, al sides and back are shaved, but the dreads around my crown are the ones that seemed to dread the fastest and even now are definitely more "dreaded" than the rest.
A bit of both. My hair thinned out quite a bit when I combed out the crochets so when I went Freeform my hair really didn't want to lock up but it did section itself. I took the sections that formed naturally and TnR'd them.
I keep meaning to do some pics or a video but keep forgetting.