I don't see what's so sad, OP
It's his life not mine. I wouldn't drive two hours one-way to go to a shitty junk shop in the middle of nowhere but certainly I've done less and worse with the better part of a morning and afternoon than his experience.
Hell, I spend a couple hours most days looking through art and antiques from dealers and auction houses and for all that I probably buy something once a month on average. Who am I to criticize some guy who likes to ride into the desert to look at granny glassware and ceramic cats?
For many people, coupled or single, part of their time not working, socializing, or sleeping is spent at what must seem to others to be horribly mundane pursuits: gee-gaw thrifting in the desert, searching online auction catalogues, watching YouTube videos of dead shopping malls, scrolling quickly past Megan Markle and Janet Jackson threads on Data lounge, cleaning the cat litter box, going to the gym...
I'm older than this guy and fell lucky to have what is, for me, an interesting life and good friends and more spontaneity and adventure than I had as a younger man, but it's not the Algonquin round table 24/7. And really, if I were to share anything about my life, I would share not the more glittering bits but the mundane, reflective parts. The one is of the moment and private, you had to be there; the other is presentation, and people will like it or not.
He's comfortable sharing his private time and reflections -- and hardly alone in that. I'm not of mind that I want to share anything branded under my own name. His content doesn't interest me, I've no desire to see more, but neither does it seem sad or some hard truth harbinger of aging (maybe of Anericans' love of their cars and driving.)
Look around, it's a world of far, far sadder shit if that's what you seek.