My 1st desktop had Windows 95 on it. It worked OK. A few years later, I bought a laptop pc with WindowsME (Millennium Edition), and it became the last Windows product I've owned. A work colleague installed Windows 2000 on that laptop, and it worked for a couple months, until I got my "blue screen of death."
At that time, they started selling the ePC notebooks, available with WindowsXP or Linux (the XanderOS) I stepped out of my comfort zone, and got the XanderOS variant, and have had Linux computers since. I'm currently using Mint on an old Panasonic CF-30, and Ubuntu on 2 laptops built by System 76.
My wife likes Mac, but I'm not a fan. My kids get a pretty rounded experience, between using their moms Mac, their dads 2 variants of Linux, and their Chromebooks at school.
Boomer: What?! Just walk into the building, go up to the receptionist or bossman, and demand to be interviewed for a job, and fill out an application form. Refuse to leave without a job offer. They'll be so impressed by your dedication, they can't do anything else, but to hire you! What are you waiting for?