Big Banks = more overlays (varies by bank)Their concern is stock price and appeasing stockholders, and because of that, their guidelines are more selective because they are trying harder to limit their default probability.  

The painting contractor leaves some behind for attic stock.

I could pay my P&I, then draw my excess Principle  from the loan.  

I know rentals are a bit different in that the renter less concerned with appeal/finishing than a buyer, but I would think the same principle would apply.

Look at external metrics like stock market, interest rates, supply and demand of homes, I'm basically looking to avoid the crash as in 2008.

It's a like a high yield (cash flow) type stock like Chevron and not a right appreciation stock (Tesla).  

If the window is single pane they should have something in stock to fix it right away.

As for property appreciation it is tough to time the market (similar to trying to time the stock market).  

I even put this number next to a 7% growth in the stock market to see how it would compare and most properties peak in their difference over the stock market around year 12-15 on a 30 year loan.Do you include the loan paydown?

Some trust real estate, some trust the stock market etc.