"The problem with selling high and buying back lower is this: the selling high is pretty easy. The buying back is very hard. Nobody knows how low it will go during the next downslope, so when do you pull the trigger and get back in? After a 5% drop? 10%? 20%? 50%? Given the uncertainty, I find I'm always back in again after only a modest drop, meaning the whole exercise left me richer but not by a meaningful amount. I guess you could wait for a drop to the modern era average multiple? Using most recent book that's 1.40 in the last decade, using peak-to-date book it's 1.38. In an untaxed account, selling know and buying then would get you a one time return of 10%, minus however much the value of a share rises in the time it takes to reach that valuation level. Not exactly a life changer."

Yeah that's the thing. I live overseas and I'm married to a non American so I can actually buy and sell in her name without tax consequences. I've always been reluctant to play this game because I have be honest- I'm just not that smart and I don't want to miss out on additional price gains. But I sure am tempted after big runups, especially now as it feels the market is getting rather exhausted. And those 5-10% gains would still be pretty good if the position is big enough and you're not paying taxes.