After soooo many questions regarding fear of the big chop, I've decided to post the response I gave to someone who wrote in to my inbox. Feel free to comment and weigh in, but also feel free to consider the Big Chop.
Why are you reticent about doing the Big Chop (BC)? I understand why many people are, but why for you specifically?
That is really the easiest way to go natural, especially if you have access to someone who knows how to style natural hair. It's the easiest method because transitioning, or growing out the relaxer, requires a lot of hard work while trying to cater to two different hair textures, and you will have quite a bit of breakage of relaxed hair the longer you transition. Your ends will need to be trimmed in inches repeatedly to accelerate the growing out process, and without synthetic hair styles (braids, weave, etc.), you will have somewhat limited styling options.
The BC allows you the time to get to know your own texture gradually and experiment with a variety of styles at each length. There are some styles that I sincerely miss wearing when my hair is longer. Had I never worn it very short, I'd never have experienced all of the ways I could flaunt my natural self.
Are you worried about how you will look with your "crown and glory"? Well, I'll tell you exactly how you'll look. You'll look just the way God created you to look--head shape and all. Go check out your baby pics and you'll see yourself. Just embrace who and how you are in all of the beauty that is placed inside of you because that's all the outside can really reflect.
After that long soliloquy, if you still want to transition gradually, I can certainly help you with that and tell you how best to go about it, but do consider the BC.
P.S. I think I'll make my response to you a blog post because you are not alone in asking this question. :-)
I would add that the most painless transition is the fastest one--the BC. The least maintenance is required as well. Really, what are you afraid of? A tiny fro is not your only option anymore.