I live in and invest in Tampa so I’m biased but you truly can’t go wrong in either market, Tampa is going to be a little better on the appreciation side and Orlando will offer slightly better cash flow opportunity whether it’s multi family, single family or short term rental.

There you will meet all the players in the game and you will get a better sense of how to move forward and make contacts along the way.

Would it be better to start a little outside the city? 

Based on your goals, experience level, and my assumption that high earning w-2s tend to be demanding of your time, I actually think that there are better ways for you to offset your w-2 income.

Storage occupancy rates during past recessions has remained relatively stableFor example, during a recession, when folks downsize from a 3 bed/1 bath to a 2 bed/1 bath, those people, historically, keep their belongings and put them in storage.Also, during inflationary times, self-storage operators can better manage rates because most leases are month-to-month.

In which case you got the tax break for them in the year you spent them (which is better).In your example the reinvestment target is to purchase 750K of real estate using $400K in cash. 

Actually, not that bad for a Class D Neighborhood, but there are so many BETTER streets in Detroit.

It means the bank has already foreclosed and they didn't sell it at the auction, either because no one bid or no one bid high enough for the bank to accept and they thought they would be better off selling direct to a buyer on the market.

Often times it is better just to part ways. 

This also leads owners to ASSUME simpler is better when it comes to management contracts.