Here are some thoughts on towing. The most important tool in towing is Turbofins. They can bring additional thrust to the tow. It doesn't matter much what boat you are towing with, except that shorter towing boats have a little better directional control at these slower speeds. To that end, the large rudder is very valuable. As you will find out, directional control of both boats at slow speed can be challenging, especially if there is any wind.
Towing under sail is generally not feasible if you're towing a heavy load, as you cannot get enough speed fast enough to gain rudder authority before blowing downwind out of control. The heavier the tow, the longer it takes to get it up to speed. Once you get it going though, it's not too hard to maintain.
The weight of the towed boat is not so critical as how clean the boat is in the water. For example, a 2000 lb. motor boat with its outboard motor raised probably has less drag than your own Hobie cart (if you forget to unplug it) in the water!
A good tower with Turbofins can generate about 50 lbs of thrust for awhile. I'm guessing that a 30' 7000 lb. sailboat can be towed at 1 to 1.5 kt by one (fit) person and 2 to 2.5 kt by a tandem (no wind, chop, tide or current), but have never tried anything that big. Your tow line can be held over your shoulder for better directional control over the tow. The advantage to that is you can tug to create some slack momentarily then accelerate briefly for better rudder authority to redirect your tow if necessary.
The bigger the towed boat, the larger the effect of wind, chop and current on the result. But if your sailboat is becalmed, a good old Mirage Drive tow might be just the thing -- sure beats a set of oars!
