Crate training older puppy

Our puppy is about 7 months now. Because I work from home I made the rookie mistake of putting the crate training on the back burner. Other than leash training which we’re currently still working on, he’s learned quite a lot and is well mannered.

I’ve started the crate training and first time I put him in, 11 minutes of solid barking and crying. Ugh my heart I’m such a softy. After a few minutes of quiet I let him out but he was attentive and honestly I’m not sure if that counted as settled or not.

Everytime I put him in there now he whimpers softly for a lil bit but eventually stops but he’s always sitting staring me down when I come back. So I’m unsure if that counts as settling. Now he isn’t starting from scratch. We gave him a good relationship with the kennel when younger so he naps in it, stores his fav toys in there, stores a snack if he’s not ready to eat it yet or jus chills in there but the moment you close that door he hates the kennel. I don’t wanna loose the progress we made but I also need him to be okay staying in the kennel for longer terms (4 hours max only! About 1-2x monthly)

He is being trained to be a medical alert service dog so honestly he’s quite well behaved otherwise. Yes I know, rookie mistake ugh! Working from home really made me mess up. My previous dogs never had issues with the kennel and were much easier to train this, I think he’s jus honestly a tad more attached than my previous dogs specially since I waited so long, or most likely cause I waited so long.

My questions are, is him sitting and attentive when I come back still counting as “settled”?

Will starting this loose progress I’ve originally had?

And lastly, with my previous dogs, I’d put some treats for them in the cage before I locked it and then walk away and come back I’d give them a single treat when I took them out (small training treat) to show that the kennel is a happy thing, and it worked well, but would that hinder progress in this situation?

Fyi he is a large breed Yorkie so he’ll grow up to be 15lbs which I know isn’t your average service dog but as he’s only meant for alert tasks, I don’t care that he’s small and cute 😆😆 (if the breed makes any difference in the answers)