Bad school district in convenient location for commute and errands for example?

After closing costs and other fees you'd likely lose money selling it.You're in a similar situation with property #2, but with more potential value on the upside.Without knowing what you pay in insurance and taxes, it's hard to know how disadvantageous your situation is currently, not to mention I'm guessing you have some kind of property management situation given the distance from your rentals.

Depending on your budget, I would recommend something within 15 minutes of the beach and located in a neighborhood that has shops, bars and restaurants within walking distance.  

Most of our properties are 2hr + commute away so they have been difficult to renovate.

And they are half the distance from the East Coast from you, although I don't know much about the ease of getting flights to Louisiana.   

The beauty of this transition is that you'll understand how the management structure works in and out so you'll be great at overseeing your projects from a distance. 

In Milwaukee, there sometimes isn't a great distance between a very good and very bad neighborhood.  

@Carolyn Fuller so my ADU is located in a working class neighborhood and we are stones throw away from the delta where there are major events like the Bass Fishing annual tour and walking distance to the local stock car events.

If you self manage you'll want something closer to home to reduce commute time, if you hire a manager then you can pick from any city without additional headache.  

What is the distance from the meter to the property?