I've put several aftermarket head units in both Jeeps and other cars. I've not experienced Apple Car Play issues with Kenwood units... that said I've not installed a single DIN in decades however my guess is the logic and software is identical between single and double DIN units.I replaced the stock head unit with a Kenwood BT-322 media player right after I got my LJ keeping the stock speakers and subwoofer setup. Sounded good and a nice enough unit, but like most single DINs, the buttons were a bit small for my fat fingers. And then I started having issues with the blue tooth connection with my iphone. I replaced it with a double DIN Sony media player head unit and have since replaced the speakers with larger Sony speakers (6.5 in the pods and 4x6 in the dash) except for the subwoofer.
From what I gather from reading online, the Kenwood has issues with playing nicely with iphones. Could be the Apple stuff not wanting to play nice with Kenwood, I don't know. Either way, I need the hands free for my phone and it was cheaper to replace the media than the phone.
I've moved away from Kenwood recently to Alpine units. Less expensive and, in my opinion, more stable and more responsive. Just opinions but ones based on recent experience.