Hi Johnathan
It sounds like you've got a pretty good setup, and the aerial photo from google maps seems like you've got options and infrastructure nearby.....fun!
I can speak somewhat to the mapping options you discussed...I've put our farm design into GIS format, available at http://www.mossbackfarm.com/archive/000179.html . GIS is very handy for design purposes, allowing different layers to be laid down, giving a good sense of landscape, traffic, and infrastructure patterns. It can greatly speed visioning and planning, without lots of erasing or mylar sheets. Especially for those of us lacking in drawing skills.
I use ESRI products, which are expensive, and fortunately for me, paid for by my employer. An open source version is QGIS (http://qgis.org/), which uses some of the same file formats, but has fewer analysis and cartographic options. Can't beat the price, though.
Alternatively, you could get in touch with the local university GIS department (http://www.du.edu/gis/ for example) and see if any students there want to take on your cause as a project.
If you're hoping to serve up the GIS data (eg. http://washims.co.washington.or.us/InterMap/InterDetails.cfm?GoNav=1) , you're looking at a more complicated and expensive system, called an Internet Map Server (IMS). You'd definitely be needing tech support far beyond my expertise in that case. One step at a time, then....
Good luck
Rich
Mossback Farm
Yamhill, OR
www.mossbackfarm.com/journal
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