When determining cost basis, the rule to follow would be to use a first in first out method, so when dollar cost averaging you want to calculate the amount of bitcoin for example that you purchased prior to Jan 2020. If you purchased all in the same place your account history should show you when your trades were made. It can definitely get sticky if you made purchases in various places but you can trace through the blockchain when each purchase was made.
RE: What do you do with a newfound sense of well-being, having wealth at your fingertips?