I am having ignition switch/actuator rod/lock rack alignment issues. Also, possibly, a worn out key lock cylinder as well.
It appears that the issues with your Jeep Cherokee are all related to the mechanical portion of the ignition switch. This switch is one of those components that gets used quite often, therefore every time you start your vehicle, and after years of repeated use, the components that make up the mechanical portion of the ignition switch begin to wear, as well as the key itself.
I would recommend enlisting the assistance of a certified mechanic, such as one from YourMechanic, to come by and have a look at the ignition switch on your Jeep. They will be able to address your Jeep’s ignition issues and make the repairs needed to allow you to start your Jeep Cherokee easily.