You don’t seem to be concerned about holding a shit ton of a single stock. From a financial planning point of view that is really not a good idea. You should already have sold your MSFT and diversified.
My position is don’t hold a shitload of stock from a single company. Period. It’s doubly bad to hold a lot in the company you work for - if the company does badly, you can lose your job and your investment. The housing question is kind of secondary and I don’t have an opinion.
You are basically describing FOMO: “what if I sell my MsFT and it appreciates a lot in the future!” The same could be said of any other stock that you are not holding now. Let me put it another way: if instead of stock shares, MSFT had given you cash, would you have gone out and purchased shares? Probably not. So why would you hold on to shares instead. For $7 you can exchange between cash and shares at any time.
Another twist perhaps. I have another house that I want to keep and rent out vs selling so that's why I'm considering dipping into the stock. Maybe I should sell the house instead of stock? I think keeping the house is better though.