I'm going to Maui for the first time in a few weeks too.
Gonna stay for almost 2 weeks, 7/30-8/10 and was considering taking the 7 and 10m. I am 165lbs.
Do I even need the 10??
I don't really know which board to take either. I have a Shinn monk 130 and mako 150. I also have a 5'9 Wilson surfboard. I love riding them all in different conditions here in SOBX but don't know which I will enjoy the most in Maui. I probably cant take them all and was thinking just the monk since its easiest to pack, and maybe rent a kitesurfboard a few days.
Also, what's the best time of day to go?
How can I find Downwinder groups? (if any)
I would take the 10. It takes up a minimal amount of extra room, but could be a session saver if the wind is light for some crazy reason.
As far as boards, I would recommend taking your Monk and leaving the surfboard at home. You can either rent or buy and then sell when you leave a surfboard when you get there. Surfboards are a dime a dozen and you will pay far less than baggage fees to take your own.
As far as connecting with folks. Just go down to Naish Beach and talk to people. The local kiters are friendly and will point you in the right direction. Just be humble and thankful and they will share the stoke with you.