New user here. My subdivision is fairly new, and a lot of it isn’t updated on the map. How often does OSM update their satellite maps?
The satellite images are not part of OSM. Microsoft Bing just allows us to use them.
http://wiki.openstreetmap.org/wiki/Bing_Maps
Maybe we will get an update, maybe not:
https://mobile.twitter.com/rbrundritt/status/821814408166850562?s=09
In the meantime, if you’re in the US, try using the USGS Large Scale Imagery.
Another US resource is TIGER, but it often updates less frequently than the Bing imagery in certain areas.
Also since you’re in the area, it’s often a good learning process to get an app for the phone and create a GPS track and add based on that.