Ok so this is a little down the road from here but assuming after the next halving and bitcoin goes into another bull run, when would be a good time to sell?
In all honesty, no one can pinpoint the exact date when the bear will come upon the market. However, we can predict the year expectedly anyway; nonetheless with the mindset that we are also in a highly speculative industry where anything is possible. The way I like to judge my prediction is to expect the bear season two years from every Bitcoin halving year. I've taken this into cognizance from my two post halving experiences and it seems to work pretty well. For instance, from my speculation based on what I just explained, the next bear after the coming halving in 2024 will begin in 2026. It happened on 2018. Repeated itself in 2022 too.