These are very important things and most of them take place on longer or much longer timescales than a few months. Early humans weren't monkeys, and after they had left the tropics, they couldn't survive without planning because getting food is difficult in winter.
Decreasingly so, thanks to climate change. The increase in temp isn't the problem. It's that climate change increases the frequency of outlier temperatures on a seasonable basis. Crops don't just fail if the average is too hot. They fail if there are too many hot/cold days in a growing season. And that is the unpredictable thing we're going to be running into in the future. Certainly while we're all alive. It's already happening.
Latin American climate refugees have been fleeing north precisely because of climate change decreasing crop yields.
Some of these things you could make yourself or were commonly self-made instead of buying, but that, too, requires planning and discipline.
I'm a bit shocked that some people think of medieval life as something like Elbonia in Dilbert comics. Heck, I even find the middle ages a pretty boring time in human history, but I know enough to understand that it wasn't as simple as "everyone lived in the mud and ate mud".
You could buy some temporary luxuries to enjoy, or save yourself a bit of labour on something you'd normally do yourself. But you couldn't really invest in your future the way we would today - everything you depended on had to be something you could make yourself, buying an implement you couldn't maintain would be setting yourself up for trouble. Increasing your productivity with tools wasn't a huge help because you always had enough labor available to hit severely diminishing returns on the land you owned. And any object of value is always at risk of being seized by the local lord or a passing army or what have you.