You know it’s funny back when I was flipping in dc pre covid, I was always amazed at the prices and in the back of my head was like I cannot believe people are paying 800-1 million to be in a tiny rowhome in a frankly pretty rough area, now of course everyone who didn’t grow up here throught it was just was the way it was, but growing up here I tried to explain to everyone just how bizzare it was that the city was so much more than then the burbs, (from 06 on there were entire areas that went up fourfold, where as the burbs were kind of flat for a decade) I won’t say I saw dc’s crash coming but it seemed so unnatural to me having grown up in the area, I also don’t think we’ve seen close to the bottom as far as urban real estate, as you said you can still trade a house in the city for one in the burbs but really given how urban living is + remote works, cities should be significantly less than an equivalent burb.

However, I would caution you on quality over quantity. 

But... that is likely to be a tiny minority.

We conditioned to ignore price, just use this tiny down and here ya go.

And only a tiny fraction has been through more than one recession. 

A mix of many assets in conservative quantities arguably is the safest way forward. 

I'm currently converting an old short school bus into a beautiful tiny home on wheels which has been keeping me very busy!

I'm sure it's happened many times over (and will continue to happen) that someone owes pennies in taxes relative to the value of the subjective property and the state takes it back over a tiny amount of unpaid property taxes. 

If someone is going to cry about their ROI% on 1 rental property over a tiny 3 year window, it shows that they have a fundamental lack of understanding of how the rental property business works.When cap rate and ROI estimates are provided,  that is a general indication of the how the average of properties in that asset class will perform over time.At any tiny window with 1 small sample size you can greatly outperform and underperform.

Then the structural engineering, any requirements such as solar, fire sprinklers, that is required  per code, and possibly  earthquake standards, (depending on location), and all the sudden that circular tiny home is a million dollar project.