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It is true that some folks will purposefully push the amount that they invest within their discretionary income to a level that is aggressive, yet they still have their other back up funds covered, in the event that they might make some miscalculations from time to time, and they also might purposefully shoot to invest towards a place that it 20% to 50% or even higher than their target just so that they are clear and comfortable that they have enough BTC.
A person who practices his system a lot will be less likely to make severe mistakes due to ongoing practices, yet at the same time, a person might not realize that he made a mistake until after he is faced with consequences of the mistake... and I would think that the more a person practices, then the more likely that the mistakes that are made are not going to end up causing any kinds of high levels of damage upon him - especially since there are always going to be trade-offs that are made, and a person can only attempt to balance trade-offs as best as he can based on his own then knowledge of the circumstances, which there are going to be known knowns, known unknowns and unknown unknowns that should be attempted to be accounted for.
But talking about aggressiveness, that is such a subjective subject. As you mentioned, if someone goes beyond their initially set target investment by maybe 20% to 50%, than whatever their target was before, we would probably consider this practice aggressive in relation to what was the investment target before.
But then when Elon Musk were to announce to invest $5 billion into BTC, would that be aggressive? It would mean he puts less than 1.2% of his wealth into BTC and that is only talking wealth as he could in theory generate tons of cashflow too.
Ultimately I think it depends on the ability to handle miscalculations or risks that could barely be anticipated. There was this one guy here who sold jewelry from his wife to go all in, I think that is a pretty aggressive approach although it could be argued that it was ok when everyone agreed to doing it. On the contrary it is hard to believe that some billionaires did (allegedly) not invest into BTC.
What's aggressive and what is not can be a wide range of factors to be considered the higher your net worth is. In the lower income ranges I think it's pretty straight forward that financial existence shouldn't be at risk, but then we all heard the stories where someone claimed to have sold their house, lived in a motorhome and won big time. But I have a hard time calling that a strategy...