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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.
You are making decent points about short term versus long term, but you are phrasing your points weirdly in terms of suggesting that the belief of not having risk is enough in order to make something less risky.. and there just seems to be problems with that way of thinking because there needs to ultimately be value in the underlying asset, rather than just your confidence or the confidence of others that the asset has value..
Let's say if we take bitcoin versus that shitcoin ethereum, and the mere fact that there are a bunch of ethtards that believe that ethereum has long term value is not going to help it when it comes crashing down.. whether that takes 3 months or it might not crash for 50 years.. but the thing is built on a house of cards.. so there needs to ultimately be value. not just confidence in the value.
The lack of risk in bitcoin does not have to do with having higher levels of confidence, but the fact that in the long run that it is actually built on a solid foundation in which it has a lot of robustness to sustain itself through a large number of attacks that could last several years or even decades, but there needs to be some actual performance within a timeline that would be acceptable to the person/entity that is doing the investing and that it has great likelihood to perform well in the long run.. whether that is 4-10 years or if it might take longer. So the confidence about the likeliness to perform well does not necessarily cause bitcoin to perform well but instead it ultimately needs to end up performing well (or not going to zero, close to zero or overall losing a lot of value) in order to not be risky.