However I have always assumed that the Detroit market will come roaring back someday (soon or in a decade or two, not sure) and I'm jealous of those who know the market well and can invest strategically.

Every part of REI involves some sort of analysis which is than followed by a strategic decision.  

A strategic interior renovation plan was immediately implemented upgrading units in-house efficiently creating significant value.

For that reason, when you begin advising others on how to spend THEIR money; you start to enter a very dangerous territory by not being careful to differentiate facts from opinions; when an opinion is warranted, it is of the utmost importance that we have an understanding - and the ability to communicate - the facts we used to formulate this opinion.I find it a bit silly to state that finding a great deal in San Diego requires luck and patience, whereas out of state, BETTER investments are readily available.

Send your spreadsheet or whatever you use as your strategic plan.  

I currently am house hacking a property (renting our main house while living in ADU) in the North and East neighborhood and strategizing on how I can buy my next one.

Outside of revenue, there are two important factors that you need to consider when you own/control many properties; asset protection and strategic tax planning.

Given your goal of holding multiple properties, leveraging the equity in your Virginia home to invest in Milwaukee could be a smart strategic move.

We believe in strategic diversification and it works when done right.

Which is why a lot of successful investors will tell you that Rich Dad got them started, but it was their own hard work and strategic initiative that made them successful.