Originally posted by pawntorook4
This is a difficult thing to get right, so no easy answer.
Calculation is very closely related to evaluation (i.e. assessment of a given position). If you can evaluate a given position with 100% confidence then you won't need to calculate any further. However, this is the exception since most positions are hard to evaluate.
In these cases we need to decide if analysing deeper will help clarify the evaluation. Many sharp tactical positions and endgame positions require thorough calculation in order to assess them correctly.
There are also many positions that are complex enough that trying to calculate further becomes too difficult due to the number of candidate moves. Here, we may have to use approaches such as intuition and risk assessment.
Finally, the early moves in a given lines are often more relevant than deeper moves. The further you calculate the more chance that something has been missed earlier. So you need to be sure that a line is forced/likely before spending effort going deeper.
I currently seldom write down lines for my RHP games. But I have done so in the past and I used ChessBase to manage the variations. I found this to be helpful for analysis, but it removed some enjoyment since the process became a bit more tedious and brute force.