It's funny. I started with a Gateway. I think it took me into the early 2000's. The next was a Toshiba. My old Satellite is probably still in the attic. I think Windows XP Pro was the last upgrade it would support. Haven't tried, but I wouldn't be surprised if it still fired up. It just didn't have the processing power I needed. The next couple machines were Dell, supplied by the company I was under contract to, so I don't know how well they held up after going back.
Anyway, when I needed a new laptop last year I ended up buying a Lenovo Yoga, mainly because it was on sale at a good price. I don't have much time on it but I like it. The tent mode makes it handy for streaming on my bedside table. It spends most of it's time in laptop or tablet mode. The only glitchy thing is that the the touch pad occasionally fails to enable to disable as it is supposed to when transitioning between modes. Not a big deal since it has a touch screen so it's easy to check or adjust settings.
I must say, I did love that old Gateway. It served me well. The Toshiba was a 17 in. Good machine too. I loved the big screen, but it was not exactly a lightweight. The Dells were fine, but felt a bit cheap to me. I guess my favorite is the Yoga. It's powerful enough for work apps (graphics and eLearning) and flexible enough for casual use.