It really doesn't matter. Sleep on whatever you're comfortable on. If that's a $60 walmart inflatable or a $4k luxury silver lined mattress, whatever gives you the best sleep is right for you.

some mattress brands offer a 30-day trial, precisely for the reason you stated.

It really depends on the style of shoe. Something like a standard running shoe is going to have to be replaced fairly soon no matter how much money you spend on it. The uppers might hold together, but the foam itself is a consumable item. It can only bounce back for so long before it won't anymore. It doesn't really look obvious, but you might start to feel weird soreness or something that lets you know it's time to replace them.

"Barefoot" running shoes with no foam, or traditional boots/shoes with leather midsoles don't have that problem, so spending more can actually let them last longer.

Skate shoes, from what I know, are basically just standard sneakers for the most part, so they will have the same problem with the foam. If you are actually using them to skate, though, you might be wearing through the sole, or the upper, and in that case, a higher quality shoe might last longer.

TL;DR, it depends how you wear through them.

I have never found a skateboard shoe that's lasted more than a year regardless of price. A solid pair of walking shoes however is very different.

I've always had a pair of these laying around for decades. I use them for walking my husky and they last about two years. They don't look great but honestly I don't care how my shoes look when I'm walking my dog.

I invested in a pair of San Antonio Shoemaker sneakers a few years ago when I started having foot problems. They are still going fairly strong. Only change was a custom insole a podiatrist made for me. No foot problems since. Highly recommended getting quality shoes.