I'm moderately anti-Windows - I think it is rarely, if ever the most optimal solution for any application. All my commercial work is undertaken using Linux, and all my personal fixed and portable devices are Apple.
However, there is no point in suffering and re-inventing the wheel just for the sake of it.
Sky Demon does a good chunk of what you are asking for and runs as both a desktop application and on a Windows CE portable. The developer is highly responsive and adds new features once a few people have expressed a desire for them.
So my hand was forced...!
I've got a netbook for planning and a cheap 7" Chinese Windows CE 6 GPS for use in flight. Screen brightness is a problem but it seems just about tolerable - I'm looking at I fashioning some kind of hood for it.