Too be perfectly honest I ve never quite understood the concept of a buddy boat. If you re not sure your boat can make it then don't go. If you go make sure you the basic spare and safety equipment
If you end up having a problem a buddy boat won't be able to do much unless you have a good tow line and conditions are calm enough. Towing a boat in open waters is not an easy job... I ve done it. Even just stopping to assist can be dangerous because of rolling motion when th proverbial you know what hit the fan
Prepare, pick the right weather window, have the right gear and enjoy