Zero money,   lived at home in Cupertino CA.. got my REal Estate license and moved out when I got a few commission checks and never looked back.. that was 42 years ago.  3 recessions.. one mini recession and a Global financial meltdown.

Look at the bigger picture and run the numbers from a GLOBAL scale rather than local scale.

University Circle, Little Italy), IF (heavy emphasis) revitalization was focused at the edges, they could / should / would spill over to improve things overall.

So it sounds like you are putting a bit more emphasis on cash flow over appreciation, which is great because I lean more towards that strategy as well.

I wish there was a place where appreciation and property taxes were tax-advantaged like a retirement account, so that my "buy" price (after I've paid my taxes on the income used to buy it) is primarily what establishes any future property taxes I would have to pay, no matter how much the asset increased in value, over my long-term ownership of the asset, so that I'm not double taxed on my income and then taxed AGAIN based on the future increased value of the asset I purchased with that income.It would be completely mind blowing if such a place existed, making that place truly unique for real estate investing, on the global stage, even so much so that a bunch of Billionaires from East Asia might want to buy those assets because they've found the best place possible to park money for long-term growth, while receiving CoC ROI for the duration of their ownership, compared to anything else on the planet Earth. 

You really need to consult with a CPA who is familiar with International Business and possibly an attorney.Given the situation you outlined, in theory, it would make the most sense to have an entity in a low/no tax jurisdiction (think trade free zones).Profits can be held in that entity and personal distributions can be made gradually.You may also want to get the advice of an asset protection attorney.Keep in mind the laws might change with the new administration but these are global business tactics used by large companies to reduce billions in corporate tax.

You'd be surprised how many businesses mostly do NOT need their people in any particular location, so why not tap the global marketplace?

This group is called he LV Global Economic Alliance.

I don't enjoy filing documents and filling out forms, so I don't do it.Another company that does this is CSC Global, although I have not personally used them.

The potential "black swan's" IMO are in federal government debt (and central banks around the world), corporate debt, and global geo-political stability, but I'm not too worried about personal debt.The largest portion of personal debt, by a long shot, is mortgage debt ... lending standards on mortgage debt are still tight by historical standards ... just ask anyone who has applied for a mortgage recently how strict underwriting is.