Ok, I'll give you a brief summary of my progression. I started with a plane that no one should really start with. A Parkzone J-3 brushless. Crashed it many times and rebuilt it many times before I became skilled enough to fly it to its limits.
Bought a Hobbyzone Super Cub and figured out it was much easier to see and control than the J-3. Also bought a Slo-V and several of the Firebird variants. Still have Slo-v and Firebird Freedom. These were fine planes, but didn't really help me progress since they are also three channel planes.
Bought my first four channel plane, a Parkzone T-28, and learned rolls, stall turns, flying inverted, etc. Crashed it and repaired it several times in the process, usually from being too close to the ground while flying inverted. Also bought a Typhoon2 and loved it, but it really didn't help my flying skills progress any more than the T-28.
About this time I also experimented with LED's and started flying all of the above mentioned planes at night. I Still enjoy this immensely.
About this time I found a local club and learned about RCuniverse. By this time I was also getting very confident with the T-28 and was already teaching other people how to fly my Super Cub and J-3.
Flew an Avistar on a buddy box at the club, joined the club, bought my own Avistar, still fly it and teach with it, also bought two more Avistars, still have them all and use them to teach.
(Not that I am encouraging you to teach if that's not your cup of tea, but teaching others also improves your own skills and reflexes. But there is a risk and a price that may not be right for you)
The Avistar and the experienced fliers at the club really helped me progress and helped my skills and reflexes improve enough to move up to more advanced sport planes. I flew a few different ones that belonged to friends before I bought my own. These "loaners" included the Sig Something Extra, Super Sportster, Tango .40, Twist .40, and some others I can't even remember.
About this time I got a simulator for christmas (FSOne) and started practicing knife edges, hovering, and other manuevers on the sim as well as letting some of my students practice on it.. I also had a friend with Real Flight and spent a lot of time practicing on it.
About this same time, I bought a Great Planes Venus .40 and a Sig Someting Extra. The Venus was stretching the limits of my abilities, so I spent a lot of time on the SSE until I got more comfortable with the speed of the Venus.
Crashed the Venus due to radio failure or some other unkown. Sold the SSE and bought an Escapade. Loved the Escapade, but missed the SSE, so I bought another SSE. Still have it, also bought another Venus and by this time had plenty of skill to fly it. I still have the Venus and fly it regularly. I'm still not an expert pattern pilot, but I really enjoy trying!
Since then I have bought and traded many planes including Extras, Edges, Yaks, just about all WWII trainers and warbirds, and too many others to list.
To this day I am still practicing and trying to improve my skills and I still crash once in a while. If you're not crashing once in a while , you probably aren't pushing yourself any. But that's fine if you enjoy where you are. Sometimes all I do is fly my 1/4 scale Cub as slow as I can up and down the center of the runway, most of the time only about 3" off the deck. Looks boring to others, but it's relaxing to me. That's what's important, do what you enjoy, don't worry about impressing anyone else!!
Hope this helps.