> What I need help with is:
>       • I can export the data out into the chunks in Shp format fairly 
> easily, I know how to script that.  And I have decent polygons for doing so.  
> I need a good tool for converting that to OSM, in bulk.

Hi Joe:  I think you are on the right track here, but I don't think you need to 
convert the shapefiles in bulk.  OSM's rather powerful editor JOSM has a plugin 
that can read (but not write) shapefiles directly.  So as long as your 
data-process pipeline converts to shapefile, just use JOSM to open these 
directly.  It is not required, but in your data import process, a good first 
step after opening in JOSM might be to write back to a file using File/Save, 
effectively "converting" from shapefile to .osm format with the simple process 
of "open, then save."  True, this is a manual process and to automate it ("in 
bulk" as you say) might prove a challenge, but the steps are here for you to 
use.

Your import page looks like a great start and so does your GitHub page.  
However, you mention there you get an error regarding WMS and I've had similar 
trouble with datasets that need a new coordinate system set up for them.  You 
might need to install GDAL (GDAL_Complete in your case) and use its ogr2ogr 
tool to convert to WGS84, OSM's native coordinate system.  If you research this 
and discover I'm correct, I can send you my "Ten Step" document that I used to 
do a similar import of US Forest Service (multi)polygons that include the 
process necessary to do the coordinate system translation.  Just ask!

Good luck with your import, (and yes, "herding cats," um, "finding helpful 
additional volunteers to help you" can be the hardest part),

SteveA
California
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