Maui is my home and lived there most all my life till my mid 40s Maui and Lanai not Kauai but its similar younger age big isle and Oahu
moved to mainland about 8 years ago sadly cause of health
or would not be here sorry not much of a mainlander as I be a island boy
some lands are closed as mentioned but once you know folks for hunting access etc..... you can go with em usually but again everything is SHORT but some are quite fun so the off road over there is really non existent as it is on the mainland as a way to travel but it does exist more to go mess around with buddies and have fun and go hunting or to surf spots etc...
never used winch or anything always plenty people pull you out kinda thing bumpers ? personal choice can be good but again not needed really
so we did a ton of off roading but not long trips like here more you go play kinda places or get to places that are not long but it does exist
as you saw from a few posts
that one you linked to with the pic of monroe trail on Lanai
I lived on Lanai back in the 90s for a while (its part of Maui county)
we always say the 6 month 1 year maybe 2 year rule applies to mainland folks most dont make it 6 months some do a year but most leave those that make it 2 might stay so we tend to be guarded not to be mean just kinda how it is but most are friendly you will find a % hate anyone from the mainland but are more forgiving if you leave the attitude at home and realize things move slow sadly its just the way it is but the majority of folks are awesome will give you the shirt off your back so dont let the few ruin it just be ready as I am sure you have read about etc...
as I say living growing up in the islands is a lot like being stuck in HS mentality till you are in your 30s and guys want to fight so get ready for the "HEY Haole you like me pound you !"
ignore em
I used to have Maui cruisers or harbor cars for just that reason total beaters you dont care about but also had nice cars Porsches and BMW etc..... car parts can be had overnight or a few days unless its a huge heavy part then it takes a while again sometimes you have to get your own in but if you get the correct person it can happen really quick
again often the slow is just to piss you off cause they can
never brought nice cars to the beach kinda thing only beaters and left the windows down and open etc... note car theft especially Toyota trucks is HUGE in the islands
like Hawaii is something like #3 in car theft in the US we had our toyota tacoma 4 door stolen pretty much everyone of my friends has had there truck stolen ! usually recovered sometimes not sometimes stripped for parts or just parked in local areas you wont go and it wont be seen by you again and used as a work truck
also note petty theft is HUGE so locked trucks often mean broken windows you learn quickly a open pick up and cooler in the bed is the norm with some 5 gallon wash containers for after water play is also common and often left alone in the back of the beds
shipping not sure what costs are anymore but its pretty common your issue will be getting from Oahu to Kauai usually on barge I imagine like it was Maui where on Maui everything shipping is owned by young brothers not sure about Kauai so if you ship make sure about the connection to Kauai from Oahu unless they do direct to Kauai ? again I was a Maui boy and each island is kinda there own when it comes to things like this never had issues shipping cars on island ever !
but my thoughts are ship a car and figure you can sell it there before you go
most my cars were from Oahu dealers and or mainland and shipped most on island want to much only exception seems to be cruisers (beater cars) so cheaper to go off island and the dealers often can ship to the outer islands pretty cheap as part of the deal
but tacos rule the island for sure most will have 6 inch lifts and tires that stick out
sure you read up depending where you work and with who basic pidgin words are good to know
even basic things like Pau (finished or done) are common used so good to know some basic ones
Keiki are your children commonly used
once you fit in over there some everyone close is aunties and uncles for sure the term you hear ohana truly fits in so when your local friends refer to you like oh go see uncle (your name) he get you a drink you know you are in with some good folks
haole is both good and bad depending on how its used so dont take it as a negative all the time
but you will learn that quickly from being there
again dont let the few jerks you will come across ruin it as most folks are cool when you get to know them and the food is awesome most locals are very funny sarcastic though so get ready for lots of teasing and stuff lots of laughing etc..
not sure what rustyfishhook ? if you like fishing you in for a treat
plenty fishing and for sure spear fishing
free diving is a part of life over there for most folks
enjoy and have fun if you can get to the other islands when you there to for sure cause Maui is no ka oi over Kauai
ahhhaahahhaah one thing many locals say you dont choose a island a island chooses you
get your local drivers lic cause often you can get Kamaaina rates for things like interisland flights and stays and stuff and even some times local discounts like %10 at places for showing local DL
best of luck man great experience even if you only make the 1 year mark at least ya tried