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I figure that hes pretty convinced that either the prolonged downward trend will reverse soon, or that his past
buying the dip type purchases were not really close to the intended bottom, so perhaps he considers making daily purchases will have less of a risk.
In the event that you have enough confidence and decide that it is a long-term investment, then no matter what price you buy it at, it will never be risky, it is only risky unless you intend to trade short term. Because bitcoin is unpredictable and this change of strategy will allow him to approach more market bottoms, he will own more bitcoins than with the old strategy.
This strategy is like someone looking at bitcoin as a savings for the future, weekly or monthly they will take some money out and buy bitcoin at any price whenever they have the money.