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Hi L, I really appreciate the bond you’ve formed with your kitty and the difficulty you’re having. I’d say you’re on the right track initially with trying short periods in the car.
One tenet to any kind of training through severe stress triggers is that you have to find a way to bring the level of stress or anxiety way down with a bad trigger. It sounds like your cat does reasonably well in a lot of situations but triggers very badly with car travel.
What you’ll really need to do is work with a vet to utilize a sedative or anxiety medication to help bring down the level of stress to a manageable level so that you can then work on some behavioral modification strategies. If you can’t bring that triggering stress down, a pet will not be receptive to training. I do think you’ll have a hard time without medication assistance based on your descriptions.
One example of a medication commonly used to reduce stress of car travel is gabapentin. A close relative to it is pregabalin, which is FDA approved for assisting cats with stressful situations.
Once you’re able to get him in a more relaxed state, try exposure to the car without driving anywhere, and only start with 5-10 minutes. Offer some high value treats. It’s a marathon, not a sprint, so you may need to continue with short periods for a few weeks. If you get the sense you’re making progress, you can gradually increase the period of time, maybe up to 30 minutes.
After that, if you feel like your cat is comfortable, you can try moving the car, but maybe only down the driveway or out of your parking lot, etc. Gradually increase the distance.
The goal can always be to remove the medication at some point if you feel like your training has been able to take over. Now, there’s no guarantee that you’ll be able to go completely medication free, especially if the car’s a big trigger, but you may be able to reduce the dosage and at least have a less stressed cat and some more freedom to travel together.