I've begun volunteering with Habitat for Humanity to gain more confidence in DIY improvements. 

@Scott Trench I think human nature makes it is easier for people to be more pessimistic than optimistic (survival bias). 

My plan is to self-manage my house hacks as long as humanly possibly.

If you are buying a property, the agent should only ask (if they do at all) to see your ID to verify your human and then only if they are providing you with access to viewing homes on your own.

Don't just learn about Real Estate, also learn about construction - go to Home Depot every Saturday and take their tiling and painting classes (for free), volunteer on a Habitat for Humanity jobsite to do cleanup and just pay attention and ask questions.

The fact is you will never know it 100% and you will get caught up in analysis paralysis which human nature finds very boring after awhile.  

Very occasionally, if the debt to income ratio is absurdly low he will tell them to pay it aggressively.

Most deals purchased in 2022 were at absurdly low cap rates and highly inflated values. 

The greatest delusion ever pulled off in human history thus far is the notion that $ goes to Wall Street to INVEST, to GROW, to RETURN, to PROFIT...... 

Maybe it's a human nature thing and I evolved from some other strain of extinct Neanderthal that made decisions based on need rather than social acceptance.