A little back story on my current situation.  Unmarried, no kids and no current properties owned.    I am an overemployed IT professional with an above average income from just 1 job.  I am 100% remote and will never see an office another day in my life.  I also currently live in Atlanta and fly free.

My focus is purely multifamily properties which severely limits my options in my current city.  Given the number of available options that each city has I am narrowing my options down to either New Orleans or Chicago.  I have ties to both cities.  Honorable mention of Baton Rouge as well.  My fiance is from Chicago which gives me people on the ground I can call on as an out of state investor when it comes to vetting things like property managers and trades people that will be needed when owning property.  Much of my family is actually from New Orleans and specifically in the construction business.  And for these reasons I also spend a lot of time in both cities as it is.

With all that said my thought process is as follows.

I am also a vet and plan on using my VA loan for the initial property purchase. Ideally a 3 to 4 unit property as 1 unit will be "called" my primary residence. I dont have any plans to move from Atlanta any time soon if at all and my fiance will be in Knoxville for at least the next 18mo finishing up her PhD. Because of my income I am unconcerned with cashflow. And to be quite honest I am not even worried about coming out of pocket so long as a sizable portion of the expenses are covered by the other units. My main goal is mortgage paydown for cashflow down the line and to build equity faster to be used in future deals as well.

As I see it the 2 cities have their good and bad.  New Orleans has the obvious weather problems.  Chicago is a tenant friendly city and state.  Either way both have excellent options.

I would love any feedback on anything I have not considered or overlooked.