There is nothing wrong with following a strategy provided the strategy is adding more Bitcoin to your portfolio. Even Michael Saylor that you referenced is following his strategy why I feel is the Dollar Cost Averaging. He also have his way of buying Bitcoin when there is serious doubts and uncertainty in the market and all the times he came out right about Bitcoin, the reason he is celebrated today as a firm believer in Bitcoin. I also use the DCA strategy which is a great way of buying Bitcoin without pressures.