I bought a used Wrangler, but took me a long time to find the right one at the right price. As already mentioned they hold their value very well. There are a lot of cream puffs out there, often called Mall Crawlers with low mileage and never been off road, then you will find the ones that have been beat up some. It's also very common to find rentals on the market too. The rentals can save money but at a risk; often they are ridden hard. If they are out of Hawaii you need to consider the rust aspect.
I've had hose of vehicles from F150s, F350, Cadi, Avalanche and my Wrangler even after 4 years is the most enjoyable vehicle I've ever had. I still look forward to driving it every day, even wit the rougher ride and lack of refinements.