I used to do a dozen two-strand twists, which I then put into a single braid. That took about 10 minutes each night. Now I do the pineapple, or as close to that as I can get (my hair actually is too short for a ponytail now). Like you, my hair kind of sticks out and holds the pineapple shape when I take it down, but spritzing it with water and wrapping random curls around my finger helps. Mostly I don't bother with second-day hair though.