I like Linux, use(d) various flavors of it, and have had experience with / exposure to it for over 20 years. But no, I’ve never had a remotely flawless experience with it on a desktop or laptop environment. Wish I could offer more help or encouragement, but figured I’d at least chime in with some emotional support by affirming that you are not alone in that experience.
I would recommend Linux to technologically adept people (ex: tech professionals, computer science students) and only indirectly to less technically proficient people in the form of suggesting something like a Steam Deck for portable PC gaming to someone who might be interested.
But for an aging parent or my best friend’s kids? No. Sometimes I already feel like I’m a free on-call 24/7 IT support tech for friends and family, and that’s with mostly Windows and Android devices that pretty much just work the way folks expect (even if that way is broken/crumby/irritating/etc).
Really depends on what the “old tech” is and who those people are, but the majority of people, the average person with average equipment, they’re not going to regret it at all.
Most of that old tech equipment is essentially just junk taking up space to the average person. Even if they had a use for it, new stuff (particularly low-end new stuff) is still relatively cheap. Like a quick peek at corporate retailer #4’s website and I see brand new tablets for less than $200 and laptops for less than $300. May not be good stuff, but generally good enough for typical non-techie users who are just simping for MAGA on Facebook while watching the Baby Yoda on their Disney+ account.