I don't know where you are from, but it's really cold and dry where I am now and glycerin + water might dry your hair out more since there is not water for the glycerin to take from the environment.
BACK TO YOUR ORIGINAL TOPIC
When you say "out" do you mean "out" as in a braid out or out as a wash and go? If I'm wearing my hair in a wash and go I have to re-moisturize every day (water + peppermint oil for smell or Jane Carter's spray leave in) since I need to fluff it back up after bed time. If I'm wearing a braid out or a twist out, I re-moisturize less because I find too many products weigh my hair down and make it less big and fluffy.
I sounds like you aren't deep conditioning enough. Maybe try increasing it to once every 2 weeks? Cut back on the henna as well (once every 2 months), depending on the head of hair, it can be extremely drying.