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Background: I'm planning to use OSM data to generate tiled maps and then serve them up as an internal service (hosting service still TBD). I want to be able to consume the tiled maps in both ArcMAP and QGIS. For my day job, I work with ESRI products. For my night job, I like QGIS.

I've tinkered with Maperitive and TileMill for generating some tiles. Both seem to be decent products. I have no preference at this time but I haven't beat on either product long enough to find weaknesses. One weakness I may have found, TileMill outputs to Web Mercator.

My question: How do I generate tiles from OSM Data and project them into a map projection created for my state? The map projection is 3071 - Wisconsin Transverse Mercator.

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If I restate your question, the problem that you are trying to solve is to have tiles in EPSG:3071.

The solution to this problem lies in creating tiles in this projection itself, rather than reprojecting existing web-mercator tiles into this projections.

For this you need two things. You need a Map server to create the images, and a Tiler to create the tiles. Mapnik & TileCache are perfect for this role. You can directly create an input file for Mapnik from TileMill.

The only semi-challenging step I see is writing the TileCache configuration file (tilecache.cfg).

I'll suggest that you have a look at documentation for TileCache, which details the parameters that you need in this file.

You can also have a look at this blogpost which shows how a tiles maps were created with a custom projection.

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