Agreed - People will purge themselves out eventually in my opinion

He eventually had 4 open-heart surgeries, was depressed, etc.Now that it is 20 years later, comparing it to my well oiled Investment property, because of my prime location, the appreciation I received is far higher than his, my cash flow is also far higher as the rents skyrocketed in my areas, AND I spent WAY less in Medical costs that he did.While I don't want to attribute all the Medical Health issue towards these difficult to manage yet higher cash flowing properties, I can see what it did to him as he would call me asking advice on what he should do.If he were to add in the medical costs and health problems, over the 20 years, I'm so glad I did not go down the high cash flow route.I can enjoy my Investments because of the lack of Stress from all these years.

If you buy a primary residence and eventually move away and delegate it if its a good asset class it will not be a problem. 

(Mchenry county area/NW Suburbs) as I've owned/lived there in the past, we have a ton of family in the area and eventually.... the goal is to turn our "side" of the duplex into a short-term rental to A.) allow us to move onto the next property/chapter of our lives and B.) we have a ton of family in CO.

Hey @Tyler Rowley, this is something that I have looked at but eventually said no and that is with me providing a boat.

You'll eventually find a good deal there if you're patient.

We eventually replaced the LVP with tile.

ARM is eventually better than IO, but IO could be a good tool if you add principal every year and "structure the payment" following 3% amortization ( I did this). 

They would lose half their income for two years, hoping that they would eventually sell it for $700,000?

The return on investment will eventually be the same as investments in other forms (stocks, bonds, or long term rentals), adjusted for respective risks.