I'm Chris Morley. I have no background in cartography, databases, server programming, or even serious bike riding.
I live in Chester and since April 2006 have been mapping mainly in Cheshire, UK. Cheshire West and Chester, one of the two administrative halves of Cheshire (after April 2009) now has all its public roads mapped and named. The area is mixed urban and rural with a population of 328,000 and an area of 917 km2. This is about the same density as England as a whole and is about 0.7% of England. There is plenty of scope for more detail here and for more mapping in the neighbouring areas of Flintshire, Wirral and Runcorn.
I use a Garmin GPS60 and now record a continuous commentary to a voice recorder (hands free on a bike). Data is transferred with GPSBabel to a Windows computer and edited with JOSM using its audio extensions.