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The always on orbit exists and is called a dawn-dusk Sun synchronous orbit. It is an orbit that is always above the terminator (line between night and day) where it can face the Sun 100% of the time.

This orbit has to rotate about a degree every day to follow the terminator as the earth orbits the Sun. It uses the equatorial bulge of the earth to achieve that rotation without have to spend rocket fuel. It is really quite interesting.

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A polar low earth orbit can be always-on (no earth shadow). Each satellite will be in thermal equilibrium, around 10°C. Catastrophic destruction from micrometeoroids is rare. I'm not saying it's a good idea, but I don't see any dealbreakers in the math/science.
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Kessler Syndrome is the biggest dealbreaker. We're already fairly far advanced in that scenario from Starlink, and competitors/scaleouts to Starlink promise to be worse.

If you plug eleventy trillion dollars of hope that the aristos can finally replace the working class into the issue, Earth loses access to low orbit from orbital debris almost immediately.

Their entire mindset cannot deal with this. Low orbit is a physically-enforced type of commons, inextricably tied to tragedy if overpopulated. You cannot privatize it and scale indefinitely. There is no defense, and any pissed off individual actor who gets malicious can burn it to the ground.

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Starlinks are in low enough orbit to passively decay in less than 5 years, that really can't meaningfully contribute to a Kessler syndrome.

Chinese mega constellations on higher orbits & their spent stages left in space are a bigger issues.

Still in case it got going & made higher orbits unusable, starlink would likely still work just fine on the lower self-cleaning orbits, not to mention using a partial (and hopefully soon full) RLV for replenishment.

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