I am thinking of running this on my vista (my only option) laptop... Will it run I'm new to GOG and wonder how it would fair on that machine.

I have a old CD (best of) of wing commander academy from years ago and I have trouble running it smoothly through dosbox (I know how to use dosbox) but my experience wasn't smooth at all...

So I was wondering, is the GOG versions of Wing Commander 1-2-3 tuned into dosbox properly so I don't have to mess with it too much?

Controller wise is my main issue, I don't have a fancy flight stick anymore (It predated USB so no go there) and I use a PS2 Controller through USB adapter, and it is a mess to configure.

Getting to the point, how stable is the GOG version of the Wing Commander series, and is it set up so I can use my joystick without any issues?

In my experience with a 360 controller, 1 ,2, & Privateer work fine from the get go, while 3 is really tricky to calibrate and even then, while useable, isn't perfect. I don't know if it will detect your PS2 controller the same way.

Also it emulates old fashion joysticks, so you will only use two buttons unless you bind keys to the controller in DOSBox or using a third party program like XPadder or Joy2key.