I followed a similar progression. Started with rubber band powered planes, then U-control, then R/C, then Ultralights, then finally certified aircraft. And now I'm building rubber band powered planes and looking at ultralights. Does this mean I'm starting over at the beginning? 
Phil 
I started with plastic scale models, then moved to RC gliders (actually, we were like the Wright Brothers because we didn't know anything about aviation and it was an age long time ago without internet, so we had to figure out what a stall was on the first flight)
then RC motorgliders, then RC planes, then real motorgliders, real planes, real helicopters and that's where I am at right now.
My company just bought an aircraft which I used to fly 10 years ago when I first started as a charter pilot, so I feel like I am going in circles as well right now

I am not sure what's next but I had been thinking about an RC tug-boat for a while.....