I was that way with cell phones for years, refused to go that route, once I did I found it a major convenience.
You don't have to upgrade every new version. My parents have had the same basic cellphone for ages now. I looked at Windows 8 for about a week, before I decided it just doesn't add enough to a desktop 'puter. But my cell phone plan allows fairly cheap upgrade every two years, so for a couple $100 why not I figure. I save by buying Dickies at Walmart. :-)
Hasn't this planned obsolescence been true for much of what's on the market, cars and trucks, appliances, etc. It generates wealth.