Honored to be elected as OSGeo Charter Member.
As an introduction, I've been working in the geospatial world ( save for short episodes with pizza, airplanes, antiquities, and copiers) since 1984. I have worked for both private contractors and government agencies. I have a BS in Geography from the University of Illinois, CU, and an MA in Geography from the University of North Carolina, CH. I've used stereoplotters ( manual and digital), done wetland photointerpretation with a stereoscope, and performed computerized mapping with open source and proprietary software on PrimeOS, VAX, UNIX ( DGUX,Solaris,HPUX) Windows and Linux. I have found open source geospatial software to be the most reliable and most flexible.
I generally like to throw large chunks of data (currently LiDAR) over a landscape scale at software to see what happens. Fortunately GRASS and other open source geospatial software seems to be fairly robust.