When we tow boats into the boat hoist at work, it's always an alongside job with at least 4 tight ropes in the required positions to maintain steerage, and reduce play when going from forward to reverse gear between the two boats.
When alongside, as long as you're set right back, and the other boat be it sailing or motor has central rudder, the tow is usually pretty good - for instance, you should be able to accurately place a boat onto a finger in a marina with no hassle, even with a decent wind.
I don't think I could even consider this at sea with a swell or any small chop, because something would get broken knowing my luck. When we towed another boat last year at sea, I think the rope was around 40ft long, and the rib being towed had its engine half way down to prevent it from swinging from side to side, and also not cause too much drag to my boat.
I always find it a great challenge to tow boats/pontoons etc... because every time is different