Of course, each of us is responsible for our own level of aggressiveness, and we should not let pressure from online or groups affect our choices in that there is nothing wrong with being aggressive as long as we do not end up overdoing it. If we overdo it, then we have to suffer the consequences, and it might be 10 years down the road that we realize that we cannot turn back the clock an hopefully we did what we were able to do without overdoing it and taking ourselves out of the game due to our own overly aggressive screw up(s).
if I may ask, how does someone really decide where to draw the line between being aggressive enough to see good gains and being too aggressive to the point it turns risky?
Being aggressive is a measure of the fraction of your discretionary income you invest into bitcoin. Being aggressive enough is of your own definition as an investor of the fraction you should use out of your total discretionary income to purchase bitcoin bearing in mind that you'll still have to build out your emergency funds and other variances of backup fund still from the same discretionary income.
Being over aggressive to a point that it turns risky is when you also involve funds that are meant for your expenses or some kind of funds you would be needing in a short while in a bid to buy more bitcoin within a given period and it becomes risky since at a closer time the supposed needs may arise and you may not have spare funds to cater for it and you end up exposing your portfolio to the risk of being tampered in order to solve such needs.