The 'base map' is OSM data? If it is then you can add the tracks you see in Bing imagery to OSM itself - so you won't need to open the Bing imagery. Saves that step and usually the base map is clearer. If the imagery is not Bing .. then it will depend on if that data is available (legally) to OSM. How long your 'base Map' takes to update to the new data depends on the app your using. If OSMand then 1 to 2 months and the data you enter into OSM should appear.