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Starting Mapping

You need some GPS traces to be sure that the Yahoo imagery is correctly aligned. I'd suggest doing the same short route three times on different days to get good position data. "basic GPS" doesn't matter.
I don't know if you have high-resolution or low-resolution Yahoo imagery for your area - low resolution is not very useful for mapping.

Showing my girlfriend how to use OpenStreetMap

this page belongs (or hides) under the Tips for Aussies section
osm.wiki/Using_JOSM
It's a selection of tips from our mailing list
Should this be expanded and linked to from the main JOSM page?

Leaving unfinished streets

I ride with sealant in my tyres. So I've done about 3 years since I had a puncture at about 5000km per annum.
Here we have nasty thorns which give you multiple punctures - that's why I fill my tyres with sealant.
Increases rolling resistance, but cuts down the time fixing tubes.