Always talk to Mechanics that work at Garages and ask them what cars do they seldom work on and that is one of the best indications of reliability and I am saying talking to more not just a few?
Second, I have done that after buying Cadillac' for years, but that is over after talking to a Part Guys that told me you can buy a Buick without all the Bell of Whistles that cost way more on a Caddy to fix!
Third, after talking to many Mechanics I have been told get the Chevy Tahoe that has 2 and 4 Wheel Drive abilities and way better than the Jeep. They are very dependable over 100,000. Additionally, I have told by many mechanics since Fiat took over Chrysler Transmissions have been less than dependable.
Fourth, the other Car I am told to look at it is Subaru Crossovers they are very dependable and seldom need repairs, but hard to find 2 year old ones so better to buy new. I am told they have some rust problems and their 4 Wheel Drive that is on all the time is not as great as expected but few repairs.
Fifth, I suggest you rent the Car you want to buy for One to Two Weeks and go everywhere, long and short trips. Sure it will be $500 or more, but you will be making an investment way above that and you should be sure you will love that car beyond a test drive. I almost bought a Volvo but took it on a Trip to a wedding in Virginia that entire week. Best move was not buying it.
If you need the bigger car go Tahoe! Almost bought an Escalade but unless you sell it in 2 or 3 years expect trouble later. Once I learned that a Tahoe would do the same as the Caddy Escalade, this is a no Brainier.
If you want to go smaller go Subaru and way better mileage. I am waiting 1 to 2 more years for better hybrids perfections.