Beginners Guide 1.1
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There are a variety of forms of gathering data for OSM:
Don't use copyrighted data
Most data that you find on the web is copyrighted, including "free" maps like Google Maps. You may never use copyrighted resources because it can cause a lot of trouble to OSM. As a rule of thumb, use no external resources except those available in the editors. If you think you found a non-copyrighted resource that isn't available in the editors, please discuss it first on the mailing list email@example.com .
What data to add
There is a lot of data that can be gathered and put into OSM: from common things such as street names right down to fine details which includes things like parks, postboxes, hedgerows, and cairns. Different people find different things more important, usually influenced by their main method of transport. If you feel it helps people find their way, then map it! A nice selection of some of the most commonly mapped features and the way to describe them in OSM can be found on the map features page. But remember you aren't limited to what is listed there, so be creative and map what is important to you!
Commonly, mappers increase the detail as they go on, but start with the basics. So the main road network tends to be a good starting point, and lesser things such as footways, or postboxes are among the final bits to be added. Again this varies greatly for different people so there is no 'one way' that it should be done.