I use an espresso machine that cost me $0 (because my housemate bought it). Prior to that I used a $0 rescued moka pot with the handle melted off, or an aeropress + porlex grinder. I bought the latter two because someone at work had both and recommended them, and I thought they would be good for camping. I have no idea if these things are "good" or not, but I enjoy the process of using them and like the way the coffee tastes.
Anything older that a week or two tastes a little weaker and is missing some (usually nice) flavours, but it's still damp and caffeinated and tasty. It's not bad in the sense that a stubbed toe is bad, only in the sense that a car snob might call your Toyota Camry bad ("common, suboptimal, plebian, old model, everyone has one"). Darker roasts are missing some flavours too, but they're often the exact ones I don't want. I trust coffee roasters to work out what suits a particular bean and know which flavours they want to keep.
I think coffee is one of those things like wine or whiskey or steak where the best way to enjoy it is to keep your mind open. That lets you work out what you, personally, enjoy. Try over- or under-extracting an espresso shot, and see how it tastes sour or bitter. Try packing the basket differently. Experiment with letting ground coffee sit for a few hours, or with freezing, or with similar beans at different ages. It's fun! You don't have to just believe someone on the internet when they tell you a dark roast is missing flavours, you can go roast your own coffee and see, or ask a roaster to do it.
If you work out what you enjoy, it lets you do enjoyment arbitrage, where you can buy a less popular bean/wine/whiskey/cut for less money and get more enjoyment out of it. If you listen to other people, you're just getting told what the fair market value of the thing is, which means you'll miss any opportunity to get a good (personal) deal.