Downside is I am unsure if we start changing zoning how much in upgrades will be required by the city such as electrical.

But do your homework; the City of Orlando (most of what people think of as Orlando isn't inside city limits) is putting new restrictions on short-term rentals starting next month I believe.

Going forward, I would do that every time you move to be able to take advantage of both your entitlement and your new opportunity without having to come out of pocket with a boatload of cash.Use BP for recommendations of decent property managers in your new cities and I would bet you find decent ones so your properties are well taken care of.Best of luckStephanie

@Matt DuboisI am a REI living in Baltimore City.

depending on the job search) until we move to the Twin Cities.

Hello,  we used to invest in FL,  my only suggestion is to stay way from 55+ properties.Many cities/regions specialize in retirement communities.  

Only rent to city people who are use to seeing rats .  

I am from Pittsburgh and it really varies from street to street and that's within the various neighborhoods in the city itself and if you are outside the city- one of the 120 municipalities in Allegheny County.  

I’ve been trying to find a good multi family to house hack, majority of them are in not the best part of the city.

Unfortunately this seems to be happening in all major Cities..