I think all your questions have been covered a few times and in a few ways in previous posts. I have 2 Islands - one of them for my wife - niether of us had any sailing experince. We love the boat.
#1 - EZ & takes 10-15min - no tools.
#2 - None required EZ forgiving, stable boat. but Still thrilling enough for avid sailer.
#3 - I truck top 2 Islands - no problem.
#4 - A wet ride in chop and wind over 12mph - some extensive posts on dogers and spray shields here somewhere.
#5 - 1 Person - Use the Hobie trax cart with the big ballon wheels. Place hull on cart, assemble Island, roll to beach, launch, have fun!
#6 - All Hobies some some sail-ability. Island is the only true sailboat (trimaran) and is the fastest kayak when not using the amas/akas & sail.
#7 - don't know -
I can tell you this much the Island is like getting 3 boats in one. I am absolutely thrilled at how well it sails & kayaks - a real blast.