I am interested in the Open Glider Network (OGN) work with a possible implementation around the Chicago area.
Looks like you found a project with a good fun to effort ratio.
The US coverage map is slim:
http://ognrange.onglide.com/#,max,re...000ff,circles;
But a tracking station looks easy:
http://wiki.glidernet.org/ogn-receiv...tware#hardware
To get coverage for a task area, you might want either a mountain top or a handful of sites?