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Nornagest comments on Be Happier - Less Wrong
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I'd suspect most people feel both stress from unemployment, and guilt when they are dependent on someone else (or possibly fear of losing this support). I can't really imagine a lot of situations where a person has months to themselves without triggering one of those two, so I'd expect most people aren't very good at evaluating the situation to begin with...
Retirement, among people with retirement savings and no major health issues yet? I'm sure that's been studied. There's also a number of professions where hiatuses of a couple months at a time are normal -- teaching comes to mind, as do the more lucrative forms of seasonal employment.
There are also people with inherited money.
There's a category I call the petty rich. They have enough money that they don't need to work, so long as they maintain a middle class or lower lifestyle. I'm not sure how many there are, but I've met a few. I've never seen them discussed or studied-- they aren't exactly conspicuous.