What is a common issue with a car like mine?
Largely oil leaks followed by various other issues. https://repairpal.com/2000-jeep-cherokee/problems
Buyers remorse
The same issue that my doctor tells me I have ; “old age”.
That it is 20 years old… and it is a Jeep…
Both are common problems that can be solved by 1) spending large sums of money or 2) buying something else.
You don’t mean Grand Cherokee, right? The 2000 Cherokee was near the end of the XJ series, and had relatively few problems. I had an '85 version, ran well for 10 years.
But no car is trouble free at 20 years.