Timbo,
The N5.5 has not been measured to the F18 Rules, so I cannot comment as to whether it would be legal. I think that adding the spinnaker gear would still leave the boat under minimum weight for the F18, but I don't know. As for the sails, that would be legal under the current Rules, however, the N5.5 mast is shorter than the Nacra F18 mast (another change) so you would have to get the Nacra F18 rig also.
The NAF18 website lists all the NAF18 Measurers and their location. Any one of those could measure a new boat or one that is not a recognized F18. Sailmakers have the option of being In House Certified. If they choose that route, they will need to contact me and I will take them through the requirements. It is not difficult, but they will need to understand how F18 measures sails. The numbers were different than North's computer model when I measured North Sails' first F18 sail.
I was not in attendance at the 2002 North Americans, however, the regatta organizers recognized the Twister as an F18 legal boat.
Ullman and North sails would have to obtain a Measurement Certificate to be class legal. A measurer would have to conduct the measurement, submit the Measurement Form to me and I have the final say in issuing a Measurement Certificate. The process is straight forward and pretty much immune to judgement errors. It is the identical process used by the IF18 Class.