Team using a big boat for first time - do we need a tender? Advice needed!

Hi, We are a team and are using a 16m boat. We have never swum with a big boat before- we are wondering if need a tender (in addition to a kayaker for the swimmer)?  Has anyone out there done this before using a bigger boat and please can you reply me with logistics tips? 1) Do we need a tender? 2) Can we swim next to the big boat the whole way, and do away with the requirement for a tender? 3) Does a second kayak work as a tender? 4) How far south is "south of the fleet"? 5) Other tips for big boats! We would greatly appreciate your advise and insight! Cat