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I'd like to get some expert opinions on how to get started in web mapping. First, a bit about my skills, then what I'd like to do.

I've got many years of experience with GIS, mapping, and cartography. And I'm pretty good with PHP, mySQL, HTML, and CSS. But I now need to bring all of that together into a web mapping project (I can't avoid it any longer!).

What I want to build is a mapping site where I can have something like a Google or Bing map base, then on top of that bring in my own township grid, and many thousands of points, with several pieces of data for each one. These points will represent wells or sampling points and will be updated monthly, and some of them will be updated daily. I'd even really like to have it so that users can add their own information to these points, and I'd really really like to have users able to draw in their own lines and polygons, and text tabels.

Is there a general type of approach to something like this?

I'm looking at Manifold [which I already use] and mapserving.com, or MapserverPro and one of the mapping packages they provide.

What about OpenLayers and embedding OL maps right into my own pages?

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