If the tow is a good bit smaller that the big boat, no need for a bridle on the big boat. Just a single line to one of the stern cleats. Asymmetric drag not a big deal. That way you can adjust the length of the tow line to get it into the most favorable spot of the wake.
And at night, you want a light on the tow. That way if you lose it, you can find it. Been there, done that. We did lose it and we did get it back under tow. Twice. LED won't kill the battery.
Tow speed is an issue. At 6-8kts the skiff will be plowing, might get over the hump at 8, depending on its weight. A heavy skiff plowing is a LOT of drag. That's why I like a light inflatable. But those can flip with enough wind.