11 Rides That Will Gain Value in 2020 According to Hagerty Published on December 18, 2019 in News by Marc-André Gauthier Photo: Gumtree 1984-2001 Jeep Chrokee Jeep has never been more popular than now and some of its classic models are gaining value. Pre-2000 Cherokees are a good example. They can be priced well above $10,000 USD.