A journey of 1000 miles starts with one step, and if you're wondering whether open source is in your future, the first step should be a trip to FOSS4G 2011 in Denver this year.
My favorite local open source geospatial success story, Pierce County, in Washington, started four years ago, when the GIS manager sent a small contingent north to attend FOSS4G 2007 in Victoria. From the knowledge and enthusiasm garnered there they have been able to start to re-make their infrastructure into a flexible mixed environment of open source and proprietary tools.
But it all starts with the basic knowledge. What's out there? Who can build with it? What are the best choices? You'll never have a more concentrated opportunity to answer all your questions about open source geospatial than FOSS4G.
I'll be there all week, teaching a workshop on PostGIS (sorry, sold out) and giving talks on introductory PostGIS and advanced PostGIS trickery.
See you all in Denver!