Does anyone know if GOG would upload ages of empire?

They need to get Microsoft on board first.

From what I've gathered Microsoft may be hesitant to release games DRM-free.

Age of Empires II HD is on Steam, so we're hoping the original comes here in the near future.

More like "fanatically opposed to".

Would be cool if GOG can get their hands on the first one.

we live in a world of hope, mostly false hope but hope none the less

Indeed... they seem to be stepping up their DRM - instead of toning it down.

Their announced console was basically to bathe in DRM before the community outraged forced them to change their mind.

I honestly think they will be among the VERY last ones to sign a deal with gog, if they ever do.