Regarding the Mac, I think you should start by describing what it is you intend to do with it. A six or seven year old Mac is certainly useful, but even simple things like wanting to install Pages or Numbers could be a show-stopper when Apple no longer provides versions compatible with older operating systems.
That's just an example, and it's not a particularly good one. Off the top of my head I don't know which macOS version is required for Apple's current Pages and Numbers apps, and it's still unclear which model MacBook Air that was. The point is that if you purchase a Mac to do specific things, make sure it's capable of doing them before you purchase it.
Your iPhone 6s for example may not be upgradable beyond its current iOS version, but that doesn't mean it's going to spontaneously stop working. It will continue to do what it always has, but the day may come when you want to install an app that requires a more recent operating system. Then you have to decide whether it's worth replacing your iPhone with a newer one simply because you want to use an app that didn't exist when you bought it.
Macs are no different, but if you want to derive a decent amount of useful life from one (knowing "decent" is something only you can define) I'd be reluctant to buy one that's older than those offered on Apple's Refurbished and Clearance pages. All of them are fully supported and indistinguishable from new. They might be older models, but some are current production ones.
The used market is certainly another alternative. You can certainly find good deals from knowledgeable, reputable sellers if you are prepared to look long enough, but it may interest you to know that sellers fitting both those criteria (knowledgeable and reputable) are rare. They're practically nonexistent on eBay for example. If you should come across one, their prices are likely to very similar to Apple's anyway. No joke — I'm often amused by people who pay more for a used Mac on eBay than what they would have paid Apple for a fully supported refurbished model.
Once in a while you'll find a private seller who wants to unload a Mac at a really attractive price. Usually that seller is totally unconcerned about money and just wants to be rid of it, but in those cases even Apple offers a trade-in value when purchasing a replacement. It's absolutely imperative to be a Mac expert when identifying such a find though.