Wrangler is no more expensive to insure compared to any other 4x4.
We have owned a variety of LandCruisers (80 Series, 75 Series Ute, 79 Series Ute, Troopy) and also a Hilux Turbo Diesel.
Recently we sold the 79 Series Cruiser ute and Purchased a Wrangler Unlimited 4 door (would love a 2 door but have a couple of kids!).
Now my Husband who is a true Landcruiser man is loving the Jeep, it certainly is easier to drive around the city as well compared to the big cruiser (parks more easily, better turning circle etc).
Yes the plastic top (haven't tried the soft top yet) does have a bit more wind noise compared to your standard car, but if you're into 4wheeling you will end up with chunky tyres anyway so if you're concerned about road noise I don't think a fourby is the right kind of car for you!
Losing value is all relative too, you will lose a similar percentage on any car when buying new, it may seem that Jeeps don't keep their value compared to Toyota but one must remember the horrendous new price that you would have paid for the Toyota to start with ( probably twice as much as you'd paid for your Jeep! ).
We looked at other fourbys like Mitsi Triton, Mazda BT50 etc, but the Wrangler is a bit more capable out of the box I reckon and it's a lot more of a fun car. And I'm impressed that when you buy new it comes with free 3yrs worth of Jeep Assist, so breakdowns shouldn't be a huge drama.
Diesel vs Petrol is a whole other debate, we've been into diesels our whole life and this is our first petrol fourby, considering petrol is mostly cheaper to buy compared to diesel as is the servicing it would take about 5yrs to break even costs wise compared to having brought a diesel vehicle and then even longer for it to be significantly more economic money wise in owning a diesel, so depends how much of a keeper your car is. (That analogy includes the fact that the initial purchase price of a petrol fourby is significantly less to start with compared to buying an equivalent diesel, the difference which can buy you a whole lot of petrol!).
We do also own an older Mitsi Lancer, it drinks half as much petrol compared to the fourby, so I think in getting any fourby the fuel consumption is the biggest thing that will hit your pocket if you do a lot of k's, followed by all the mods you will ultimately want to do...suspension upgrades, tyres / wheels, spotties etc!
I hope my kids want a fourby when they grow up, better than hooning in some sports car (not necessarily safer just better
). Just like when it comes to bikes, in an ideal world you'd be able to own one of each!