Well, if they are just noisy or run rough, you can try to clean them out and relube them.
But if they've gotten too loose and wobbly, you'll have to replace them.
Clean & lube can be a bit difficult, so some prefer simply to replace.
Yes. When they make noise when you spin the wheel. Also if you see dirt in your wheels you should replace them. Also they only cost a few bucks so what the heck. You mine as well replace them. I like to because i go faster. i ve been Skateboarding for 6 yrs. now
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Depends on what you mean by "good", how you skate, and how much time/money you want to spend on maintaining your stuff.
"Fast" bearings usually don't last very long. They tend to be sensitive to getting dirt/grit inside, which cause them to wear out fast. Not a good thing if you ride outside unless you're OK with replacing them often.
Sometimes it's overall better to use a poorer but cheaper bearing. You can afford to replace them more often, so you get to ride on "new" bearings more often.
And a new cheaper bearing is probably better than an expensive, worn-out bearing.
Whenever they begin to get noisy and/or begin to feel notchy - don't move smoothly - when you turn the wheel with your fingers.