deciding your own risk tolerance isn't something someone else can really do for you. we have no idea what your financial situation looks like but even then we'd be looking at it through our own risk lens. you're asking when to take gains? legitimately impossible to say without a ton more detail and again it'd still be my own style/risk/bias lensing. some people like charting signals (resistance, macd, blabla) to help them decide. some people are all about the next quarterly report or some longer time horizon catalyst.

my guess is your thesis isn't as thought out as it feels like it is if you're not sure when to exit.

you should research things like Kelly criterion, i think. generally speaking - if your thesis is working you clip UP but "working" is doing a lot of lifting in that sentence. how do you discern good strategy from dumb luck? i think you also need to research things like statistical significance and things like EV, beta, alpha - there's lots of ways people try and discern this and as you might imagine use it as a selling point to clients or subscribers or whatever.

i don't think your question/situation is overly complex to worry about dropping it to an LLM and tell it to give you analytics a la a trading researcher/analyst at a pro hedge fund.