Will,
It is kind of late for this w/e but if you want to start a trial Sailchart you can try this:
Go to Program Data>Expedition>Sails> Sailchart.txt

Open it with MS or Open Office etc
save the file as "SailchartNotso.txt"
Trying to stay within the format of the file make changes reflecting the limits of Notso's sails
eg the upper limit of your J1 in terms of angle and WS

Start with a simple change and keep going until you have the limits of all NotSo's sails

After making a change save the file back to ProgramData and go into Exp and open it from the Sail tab > SailChart button

The long term goal is to get the range of each sail's data according to your observations in practice and as 'claimed' by the sailmaker.  If you have a good relation with a sailmaker they may give you a graphic crossover chart for sails you bought from them.

Then when you run an Optimization it will reflect in the results 'which sail' it will take some trial and error til it gets close to what you want.

Good luck in the TransSup
and welcome to the forum,
Ernie M