Even 2 months old can be outdated (e.g. can be missing houses built since, or showing houses that no longer exist). In some areas, this can be a very significant effect.
My point was that OSM data can be much more accurate than the imagery. Or not, depending on location.
I'm sure you can use the newest/best data for your company because you can pass on the costs to your clients.
In the "high spatial resolution" - i.e. 50 cm per pixel or less the well-known providers everyone is using are Digital Globe, Airbus or Nearmap. Above 50 cm it starts to get hard to confidently see enough detail.
Google maps terms of service actually prohibits using satellite imagery for feature extraction ( https://cloud.google.com/maps-platform/terms/ ).
Bing is the best on the cheap end. Actually, Bing donated imagery for OSM mapping purposes ( https://wiki.openstreetmap.org/wiki/Bing_Maps#Bing_Aerial_Im... ).
Shameless plug: At tensorflight.com we have deep learning models that can do just that.