What is the point behind having paid off real estate, if you lose it later in life to oppressive taxes?

I had false beliefs that it takes money to make money my whole life.

You can also take a car ride and travel to Dallas, Houston or Austin.I think NYC is a good city if you want to work and make a lot of money. 

Assuming property taxes + insurance added don't go above $1,100 total, you could maybe make this work. 

So as a newer person in an area if you want a lot of bids before you close you'll normally end up with the more expensive guys or the ones that don't have work at the moment (usually for a reason).

It starts with doing 10-20% of the work and paying much lower taxes.

This will give you clarity on the numbers and help you determine how to structure an offer that works for both sides.

Literally the same thing everyone has said to me my entire life about why you shouldn't buy real estate now.    

This requires an income that allows you to maintain your standard of living throughout your life.

The 80/20 rule applies to most things in life but in Portland real estate it’s more like the 90/10 rule...10% of the agents do 90% of the work.