i think you have the point to decide when the right time to pull out your investment because its all about how much you want to take profit in crypto. my suggestion is don't be greedy when you can take the highest profit because the price will be drop suddenly and you only can take small profit. its happen to me in the past so i think its better if you have a set price on how much you wan to sell and take that profit.
Yes, sometimes greed can be bad. Rather than expecting price to rise better take out initial investment and sell only those coins. Rest all can keep for rolling. As fluctuation can totally shatter the market.