I like going used for the first plane. I do recommend having an experienced person go with you or have the guy demonstrate everything works for you. Here are some links from your local CL.

http://greenbay.craigslist.org/tag/3090909094.html - this guy has an Alpha 40 w/transmitter for $190

http://greenbay.craigslist.org/tag/3045643247.html - this guy has a foam/electric Super Cub ready to fly for $130

http://milwaukee.craigslist.org/tag/3047398976.html - this guy has a couple

http://milwaukee.craigslist.org/tag/3075396286.html - this might be a good deal but a little small

http://milwaukee.craigslist.org/bar/3073056364.html - this guy has an Avistar (one ofmy favorites) for $125

http://milwaukee.craigslist.org/tag/3101128326.html - this guy has a couple of trainers; if you can get him to split the package

http://milwaukee.craigslist.org/tag/3106426481.html - this guy has a ton of planes for sale; you should talk to someone like this to get the propper start

http://milwaukee.craigslist.org/tag/3083689266.html - $150; looks like everything you need

http://milwaukee.craigslist.org/tag/3103711875.html - looks like some good stuff here