With that perspective buying a bit more expensive or cheaper now doesn't matter, what you have to buy is as much as you can when you get the money for it.
I meant something similar: the important issue seems to be that it's easier for Microstrategy to get liquidity to buy Bitcoin in bullish phases. It doesn't matter that much if he's very long term oriented like he says, or if his horizon is (secretly) a bit closer in the future, e.g. late 2020s.
The big problem of this strategy is however that it makes MSTR also vulnerable to short-term price swings because they always will buy above the average price. Let's say we have a crash in late 2025 and 2026. MSTR has already survived the 2022 crash, but there were fears of bankruptcy at one point if I remember correctly and MSTR suffered in this phase. Now let's suppose that the crash in 2026 is slightly deeper than the one in 2022. If things play out badly, the high cost of the Bitcoins Saylor bought in late 2024 and 2025 could then become a problem. If the investors demand repayment in cash of their bonds, then he may be forced to sell BTC for a loss, dipping the market further.
I can however not imagine a solution for the problem. He can't simply say: "okay, I'll buy the dips only", because he also doesn't know when and if dips happen. And if he retains the income from his notes and hodls them until the next bear market then for sure this will not be as attractive "story" for the investors. "It can only go up from now on" sells better.
In conclusion, the "rules" of the stock market (your company is higher valued when the prospects are good and thus you have more liquidity) limit the possible profitability of the MSTR model, which would be higher if he was able to buy more BTC in low-price phases, and make it also more risky. Thus I'm not really convinced of the model, it may even be an accelerator of one of the next crypto bear markets if Microstrategy is forced to sell BTC eventually.
I don't quite see why he puts his common stocks as a hedge and not bitcoin itself.
Because the post is pure marketing and not scientific (he benefits more from MSTR increases than from BTC increases)? For me the post isn't specially "deep". I however have some doubts about the legality of such a style of communication ...