I had moments when I wished I didn't have to go that low (less than an inch), however, I never really regretted the decision to let it go and start over fresh. The biggest challenge for me was 1) getting used to seeing myself with hair THAT short...I'd gone short before (think halle), but this was a different thing for me and 2) finding what works for MY HAIR...it wasn't until I actually started paying attention to the top 5 ingredients in products that my hair responds well to that I found myself moving away from the whole PJ thing. Yes, I still like trying new stuff, but I'm not a bandwagon type of chick.
Unlike a lot of naturals who tell everyone to just BC already, I say, I can understand how that's not for everybody. When you get fed up with transistioning and you've mentally prepared yourself for different styling options, etc, then, you're ready....don't do it until YOU'RE READY.
ETA: The longer you're natural, the greater the chances are that you'll stay that way. I like straightening every now and then, but, big hair is what looks best on me now. My fiance even prefers my curly mane to my straightened hair.