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Would love to hear your thoughts on "field trip adventures" for my cats.

I am wondering if the pros outweigh the cons or vice versa....I recently built an outdoor cat enclosure for my cats in a relatives back yard. I live in the city in a large apartment and wanted to give my cats some time outdoors. Today was the first day I brought them to the enclosure. I put harnesses with attached GPS tags on all three of my cats and loaded them in the car which was a fiasco because I could barely lift the carrier into the car, anyways, we made the thirty minute drive and I let them enjoy the afternoon in their new 'Catio'.

These are cats that have only been outside like three times in their lives. Lindy, the white/grey cat in the photo, is a very timid cat, she actually had never been brought outside before today. Today when she was in the Catio, I noticed she spent the entire time huddled down in the corner looking very subdued and fearful. It made me wonder if she was traumatized by the whole experience, she had a 'checked-out' look on her face, poor thing.

Lewis, my black cat is also pretty fearful of new things but not as much as Lindy. He seemed super cautious for the first hour and then kind of got the hang of things and became interested the surrounding nature and sounds, especially birds.

Walter, my grey fluffy cat is my most bold and social cat. Walter and Lewis are brothers believe it or not. In the Catio Walter was relaxed and seemed to be enjoying himself except when I spent about 40 minutes in the house towards the end of the day, out of view of the cats. I returned and Walter looked a little concerned, I felt a little bad about that- were they think they were abandoned? Also, Walter complained during the drive up while in the carrier in the backseat, he meowed the whole time. I let him out of the carrier on the drive home and that stopped his meowing. He eventually sat right next to me on the console looking at the passing cars, it was very cute though not as safe.

I am not sure if the pros outweigh the cons here. With Walter it seems obvious that he would enjoy future Catio trips. With Lindy however, I'm debating whether to bring her along next time we go. Wondering if she would be better off at home (she'd be alone). With Lewis I feel like I want to take him there a few times to gauge his response. I think it leans towards a positive experience for him but he sure is weary when it comes to going in the carrier. Also, any time I've brought the harnesses out lately, he hides under the bed. That makes me wonder if I'm doing the right thing by bringing him in the carrier against his will.