Towing isn't that hard just have to keep an eye on every thing thats going on. you could have a 100' tow line but unless your a assist boat you don't keep that on board like we do. you want the boat about 80-100' away that gives you plenty of room between the vessels incase your motor was to die too. Also there two ways to tow when towing for long distances you tow from the stern. theres two ways you can tow from the stern from a bridal to keep the tow rope in the middle of the stern or you can tow from one of the stern cleats if it is well supported. for a sailboat a bridal would be better off.
Also when you get into a harbor or place with other boats you start to tow from the hip. you hook up like as if you were to keep your boat at the dock but your boat being the dock and the other boat being the boat tieing to the dock. this will give you the ability to stop the other boat and safely manaver it.
Also i wouldn't recomend towing from winches keep all your ropes at the stern and keep a knife redially acesseible to cut incase something happens save your boat over the the boat your towing. you can always help them out after there boat sinks not if both are sunken. also when towing sailboats and powerboats. you keep all steering controls centered and do not touch them when towing. your in control not the boat being towed. i have some experiience towing. so this all stuff i was tought how to tow safely. Also just rememeber your not forced to tow that boat or put your self in danger.
16' mistral sailboat, And 27' coronado