I understand b/c I am now currently relaxed and don't see myself stopping anytime soon. Yes, there are many here on this board who love curls, and so do I, just not on my head.

I was natural for 3 yrs when I realised that even though my curls looked great, and my hair had looked better than I had ever thought, I just couldn't love my curls on me! Somehow I just couldn't get my mental image of myself to mesh with the curls especially since my hair turned out to be curlier than I had ever remembered it being as a child.

If this is how you feel as well, then do what makes you happy. If your simply thinking about relaxing just to be able to make you hair more manageable, then I would experiment more. Right now I am trying to stretch my relaxer a bit more, but taming the new growth is becoming a bit more difficult (but still easier than flat ironing my hair everyday! Xp). Do you really want to go back to that?

Even I recently had to hunker down and experiment more with my hair to resolve and issue that had plagued me for as long as I could remember. The result was that I found my hair needed more conditioning as opposed to more moisture and/or oils.

I found the only way that I could achieve this was by using a RO conditioner as a LI. All of the products I tried that were marketed as a LI just wasn't enough. Perhaps this might help you as well?

Another thought: You say you condtion/DC alot, but does this include protein treatments as well? Sometimes a lack of protein can inhibit retention of moisture as well.
Very fine, high porosity, currently dyed and growing out the relaxed portions. I'm pretty sure my hair's 3b something IIRC. We will be finding out for sure as time goes by.