I try to pre-wire when I can. But with using T-stands, it's not as practical.
With my 8 64 LED Pros, they go 4 to a T-Bar, and they stay mounted on the bar and pre-wired so all they have to do is get lifted up and are good to go.
My Mega Panels stay on a 5-foot section of i-beam trussing and are floor mounted, and stay pre-wired as well.
In your case, I don't see how safe transport would be possible with leaving stuff on the stands.
Don't forget, if your pole is 1.5", why not pole mount a light or two? Nobody said the light has to go on an arm or bar!