I looked into the success of different countries' quarantines. New Zealand had both the best implementation and the best data, so I draw most of my conclusions from them. With a 14 day quarantine (testing on day 3 and 12), New Zealand had a "barely visible on the graph" number of import-adjacent infections. But according to a statistical model, these are caused by infections caught during quarantine (i.e. a couple with one infected member quarantines together, the second member catches it on day 7, leaves after an effective quarantine of only 7 days, then spreads it in the wild), so if people are completely isolated and occasionally tested, 14 days in indeed sufficient


Worth pointing out that if we quarantine for X days and do not actually test, relying on symptoms, then we are selecting for slow incubation and/or mild/no symptoms before X days.
A key question for people figuring out good longterm isolation practices is "how long do I have to be symptom-free before I'm 'certified safe'?"
This post on the typical-course-of-COVID-19 provides some studies that inform on the question, but doesn't directly answer it yet.
I recall hearing something like "most cases last less than two weeks", but I'm not sure if two weeks is actually a strong enough upper bound that I'd feel comfortable encouraging lots of people to act on it.
This contains two subquestions:
(I'm personally most interested in the answer to the second question right now, but both seem important)