As a staff member at our local club, I've had to 'rescue' Sunfish a couple times using my Hobie 14 Turbo as a 'Tow Truck', tacking with another boat in tow is a Pain!!! Does anybody have suggestions to make it easier in the future?

Use 2 tow boats. H14 turbos are not the best fit this- too small.
I have towed a dead 16 foot powerboat sucessfully in the ocean with 2 Hobie 18s-- 6 miles to weather. We used a long tow line and a shorter tow line. When tacking, the inside boat had to pull up its boards and rudders, but it worked great. We even beat one of our Hobie 14 sailors back to the Cedar Key, Florida Beach.

its a good idea to make a bridal for the tow line so the other boat doesn't pull you backwards in a tack...

also its a good idea to rig the tow line with a quick release knot if you can so you can "dump" the other boat if you need to

It would make a difference in towing technique depending on whether the towed boat has a person aboard who is able to steer his boat.

If that is the case, when the tow boat wants to tack, let's say from port tack to starboard tack, the boat in tow could steer to the right, which would help pull the stern of the tow boat to the right and actually help the tack. Correct?

I DO know that a Laser can successfully tow a disabled Hobie skiff powerboat. Don't ask me how I know.

Use a very very long towline