Personally I went through a lot of the same considerations and the indecision and flip flopping got quite tiring.

Eventually I just simplified things. Living in a property you own gives so much more for your money compared to what one could afford at the same level renting. And on a long enough timeline crashes have had minimal impact. Many of those disruptions would affect the financial markets too so unless you’re extremely conservative leaving the money in stocks is not very safe either. I’m not renting for another 5 to 15 years with a small place and a nosey landlord jacking up rent regularly. So I bought.