Before we begin to imagine if Microstrategy and Michael saylor will their bitcoin stash in this coming bull cycle, lets first find out how big this company is and whether they will be needing a huge amout of money for any reason in the near future, considering if this is a question, I would say "NO", Microstrategy is a pretty big company with lots of money at their disposal, I personally think that their investment in bitcoin is for now, considered as their foreign reserve, that is, their way of saving funds they don't intend using for any thing in the short or long term, so, for this reason, I do not think Microstrategy will sell their bitcoin in the coming bull cycle, but on the other hand, even if they decide to sell, it's their money and I believe that there will be more than enough liquidity in the market in this coming bull cycle to absorb such huge sell off without it significantly affecting the over all market condition.
And No, I don't consider this things when making investment decisions, the market is big enough to give everyone patient enough big profit.