A:Answer A game would have to have Xbox controller support for it to work. I'd assume something like ilomilo plus would, but don't actually know for sure.
An Xbox live account has nothing to do with whether a game supports a controller or not. Controller support is entirely up to the developer to add if it makes sense.
Also, an Xbox Live account is free anyway to sign up for. It's only the 'gold' level of service that costs money, and that's mostly for the Xbox. Not sure if having Gold would get you anything on a PC/Surface.
Regardless, controller support is up to the developer of a game, it has nothing to do with whether you have an Xbox live account at all, or whether it's silver or gold