Find a local flying club and join. They will point you in the right direction and get you started.
A kit is a good way to start, but your budget won't get you everything you need. With all hardware and covering a $100 kit will be closer to $150 to finish, then you need an engine and a radio.
There are some smaller trainers, but I'd get at least a .40 size trainer, they are more stable and easier to see.
The guys at your local field might sell a used trainer to you.
I'd sell you mine - Hobbico Superstar with .40 OS and 72 Mhz radio, looks like new and has no more then 2 hours on it - how about $150?
Shipping would be too expensive, that's the dilemma with planes. Check the ads here on RCU or Craigslist to find something local.
A very good investment is a simulator like Real Flight, it costs some money, but it saves you a lot in the long run.
And you might consider getting an arf - http://www.valuehobby.com/airplanes/...-series-1.html
Or this: http://www.valuehobby.com/airplanes/stik-series.html
It's a tail dragger, but very easy to fly and steer on the ground. I have the .60 size with a gas engine and you can slow it down to walking speed, it's very stable and makes a great trainer. And the pirce is right, great quality