well, you technically never need to cash out; depending on the stocks that you buy. If you buy Nvidia or Tesla, you might want to get in and out, but I never play that stuff. I buy old boring stocks that just grind income. I own a lot of Altria stock symbol 'MO'. Yes they make Marlboro cigarettes, they own a big chunk of ABinbev (budweiser) and a bunch of other crap. Right now they issue a dividend (send you a check) every quarter that works out to about 9.6%/yr based on today's stock price. The dividends are 'qualified' so if your AGI is under around $80k (depending on married/kids, etc) you pay 0% capital gains tax on the dividends. Even if you are over that, you only pay 15% fed tax up to around $400k of qualified dividend income. You get that income for the rest of your life and they raise the amount a little bit every year.......
Not trying to get you to invest in MO; just trying to talk you out of a $630k moho :))