Microsoft only provide out of date OpenGL headers because... well they are monopoly and get to make it hard for competitors to work well on Windows.
There are workarounds, and the OSG builds these in so where the modern OpenGL features are missing from the headers the OSG defines these automatically for you, and also at runtime queries for the modern features+extensions, this means you can effectively use all the features of the hardware without worrying about the limitations of what Microsoft provides.
The properties dialog you provide doesn't mention that actual hardware you have so there is no way for me to provide advice on just how capable it is. All modern hardware is capable of running quite advanced OpenGL features, included embedded GPUs, some OpenGL drivers provided by the hardware manufactures can be a buggy though.
Mostly I think you should be OK, just try our applications that have the features you want and if they work on your hardware you are good to go. If you hardware is a real limit that using a add in card from NVidia or AMD is a way to go.
Cheers,
Robert.