Domicile: WA State (income tax free)Property location (Texas): (income tax free)LT gains + Depreciation recapture ~ $300k on a $500k income property ~effective / average tax rate = 12% for past umpteen yrs (relatively low income, avoiding IRMAA and doing Roth rolls (no 'realized' income, just transferring from tIRA to Roth = vast majority of annual MAGI income)In the end (coming soon, ~17 yrs) ALL remaining estate will go to charities / Charitable Foundation / DAF.

Each of them sought the property for their primary purpose of worship/office/etc, and then sought out additional uses as well - nursery school, food bank, place of worship for a Jewish congregation (Saturday versus Sunday), auxiliary space for the local library that needed additional educational space, counseling, etc.There is merit to your concept, but many factors come into consideration:  zoning, parking, how easy it is to "convert" space, etc. 

Woodlawn is seeing some price increases lately due to new investment and the Obama library.

BiggerPockets has a whole library of books that are extremely helpful.

But getting a vast majority of your bookings from a single platform is also a HUGE risk that most people ignore because times are still good.

The vast majority of units is (over 60% of all doors) is owned by only 3% of landlords (choke on that Vilfredo Pareto!)

Humboldt Park also has a lot of good deals.Don't overlook the South Side either - Woodlawn has seen a massive resurgence in the last couple years with the Obama library construction. 

A vast majority of appraisals are valuing the ADUs less than the hands off cost of adding the ADU.  

I'm excited to learn and grow and eventually contribute to the vast knowledge here. 

With the simple understanding that these are agency representation marketing/sales, James Wise is vastly raising the bar on information disclosure.