Charlotte could be an easier transition in terms of population and infrastructure, but not necessarily in terms of personal interest, and culture. 

It’s out at Resident Culture.

I used to live in celebration Fl near Disney and man those houses are crazy expensive 

Each city will have its own culture, and sellers will respond to different marketing efforts differently.

We live in a world where the media celebrates the lottery winner instead of the business man/woman. 

When is Tenant Appreciation day and do you celebrate?

@Nick Bleser In B&H the two biggest external risks are:(A) a decrease in demand and (B) a change in neighborhood desirabilityIn both cases, your revenue is threatened AND there's a potential need to increase expenditures - there isn't much you can do about it.Apply that to market cycles, and you're assuming risk if a cycle is likely to decrease rental demand ... because fewer people will want to culturally rent, because there will be more supply, or because there's a declining population IN THAT AREA.  

I hope I can also be in a similar position to celebrate in the next couple of years.

Split the profits with your partner and celebrate!

Now, be mindful though, don't celebrate too much that you forget to do work now.