Hi TJ,
My transition into more minimal footwear was just that. A transition that was quite gradual. When I was a freshman in high school and starting up with track and field, I got a pretty poor fitting at a shoe store. I'm not sure what this lady was on, my arches are more rigid than an aqueduct, but she warned that I was on a path of imminent self-destruction if I did not wear the Brooks Adrenaline.
Fast forward about seven years and dozens of injuries and aches and pains, I graduated from college right as the bottom dropped out of the economy and I ended up working in a running shoe store. I realized that I was in the wrong footwear for my feet, so I switched into neutral trainers. These were still pretty bulky in the heels: the Mizuno Wave Creation, a plastic monstrosity of a shoe and the much more sane Mizuno Wave Rider.
This certainly helped but after another couple months of training the usual hip and groin injuries (the recurring injuries of the past couple years) returned. I was really very close to just chucking my shoes out the window and taking up backgammon, but by chance I happened to watch Evolution Running, a DVD by Ken Mierke. It is certainly worth checking out as believe watching it was the first positive step I took to finally running well.
I started trying to take shorter steps and land more midfoot/forefoot and even in my Wave Riders the effect was almost immediate. It was as if I had been forcing myself to breath through a straw for eight years and then frustrated, I finally spit the damn thing out and took a big, deep breath.
But, like I said it has been a gradual transition. Plastic cushioning systems aside, I love the way Mizuno uppers fit my foot, so I bought a pair of Wave Precisions (marketed as performance trainers) and a pair of Nike Haywards. Then I tried the Brooks Ghost and then started sprinkling in the use of a racing flat, the Mizuno Wave Ronin. I also kept a few pairs of Nike Pegasus (Pegasi?)for use on recovery days.
This occurred over about two years, so please don't think I rushed into things. I realized my feet never really hurt at all after working out or racing in flats, so it was the next logical step. I live in an urban area, so I'm hesitant to actually run barefoot. As liberating as barefoot running feels, I really don't want to have to be constantly worrying about the glass and rocks in the roads I run on. Alas, I wonder if this makes me an hypocrite or will provide fodder for such accusations (especially in the other minimalist debate thread
http://www.letsrun.com/forum/flat_read.php?thread=3130011&page=0
). I usually limit my actual barefoot running to strides and some loops in a grassy park near my house. Other than that, I try to do the next best thing with low-profile shoes. Lately I have been using the Ronins, the adizero Ace and Aegis, Saucony Type A2's, Gel Hyperspeeds, and am experimenting a bit with a pair of Newtons.
I still work in a running store, so I will occasionally run in a more substantial shoe that is seeded to the employees. They feel a bit clunky and are a bit of a crutch, but it helps me understand the shoes I am selling a bit better.
In a nutshell, I made the transition over a couple years, decreasing the amount of midsole between my foot and the ground every few months. I did not have a master plan at the outset, but it has seemed to work really well for me.