I have received a range of estimates on the cost and value of renovations and upgrades, and I figure I can safely predict that any renovations/upgrades will "break even" from a sale perspective, but are not likely to increase the value of my house much over and above the cost of said renovations/upgrades.

Closing cost items such as a escrow fees, title fees, lender fees, appraisal are better able to be predicted and that is what you can compare from one lender to the next.  

Nobody can predict that eventuality with cetainty.

"Higher risk"- maybe but it depends on what that means to you and it is difficult to say what will happen in the market (as it always is- nobody can predict it with certainty).

Following Hurricane Ian, insurance rates are predicted to go up by 20%-40% in the next year.Over four years later, we're still recovering from Hurricane Michael, a Cat 5 that is the fourth strongest recorded storm to ever hit the U.S. 

Right now we are in a difficult market and I predict it will become more difficult before it gets easier. 

The big lumps of cash come at a price, and do not always come at a predicted time if your business systems are not dialed in.If purchased right properties can give monthly cashflow with a little less work.

I mean we all “should” care but good luck predicting two decades from now.

I would think that's a speculation, just as any investor "predicts" that the area is the next upcoming neighborhood.

v=LS879r7xeLc&feature=g-all-uHe also predicts another housing bubble so maybe this is all our q's to get ready to make a lot of money?