My wife is what I would consider fairly supportive but doesn't quite buy into real estate, and is  averse in general which creates psychological road blocks that I need to contend with. 

If you're the type that pays various handymen to fix things as you go and never really cares to learn how a building or a house operates, what it needs as periodic maintenance, what its weak and strong points are -- fixing old properties can easily turn into Whac-a-Mole and cost three or four times what it should.On the people side: after doing this for long enough, I've come to understand that not everyone is psychologically cut out to be a landlord and deal with tenants all day long.

It's called "psychologically disadvantaging" a property. 

So it's really just psychological comfort vs math. 

Bad timing in a turbulent stock market can set you back for years before breaking even, and if you happen to need to sell some stocks during a market correction to pay bills, that can be very destabilizing…both financially and psychologically.

It’s almost like war in a psychological sense.

The psychology of the confluence and flow between desired active returns, vs desired passive returns, and industry created expectations is a really fascinating study.  

As long as one pays rent, the anchor will slowing or prevent the boat from moving far, either physically, psychologically, or both...

The psychology of the deal.

But recently it's taking a toll on me psychologically and I'm wondering if gambling is really for me but either if I keep playing poker or not I need to find something more productive to do with my earnings.