Sounds as though Kashi values the relationship and that is the most important thing for him when working with you, does that sound right? I think he is trying to help you in ways that he probably isn't insured for. Is he a CBT therapist?
Kashi is well meaning but this is sending out all sorts of weird signals to you and has you wondering what is going on between you, something has changed, boundaries have been crossed.
I am wondering if there was an accident when you were out with him driving and you couldn't sue, what would happen to your relationship?
What is your gut instinct around his sudden change of mind, my guess is you are feeling something isn't right, something has changed. It may be well meaning but it has changed things and this could be discussed with him. Do you think you could talk about the consequences of his gesture ?
As most people know my therapeutic relationship went south and this was because t crossed my boundaries, it was in a well meaning way. Letting me see her late at night, bringing me to places she worked, disclosing lots of personal details about her life. It all lead to me feeling very confused about my ts intentions and motivations. I ended up being her therapist in a lot of our sessions. I am not saying that this will happen with you and Kashi but these boundary crossings happen so quickly that sometimes they are part of the norm before you know it you are friends.
I am very ethical and knew that what my t was doing was extremely wrong but our relationship was too important to me to let go. I was lonely.
I don't think t thought she was breaking any rules either, she thought it was helping me but it wasn't because I left feeling used and confused.
I know this is not your relationship with Kashi but your sense is something isn't right?
Can you talk to Kashi about this and what his intentions and motivations are by breaking his own boundary and risking his insurance liability by bringing you out driving?