A good step one is having a meeting with City Planning & Zoning staff. 

Challenges?

It was not the best location and a lot of challenges.

House hacking was a great stepping stone to buying a single family and couldn't recommend in more highly. 

Without Disney Orlando is gong to be a bit a challenge but I feel like we are making some progress.

(Im able to get into this thing for only 10K the cash on cash return is absurd from 37-56% (depending on closing paid and points i pay, its an 8% Cap, 350 cashflow (after variable expenses) Brand new.. seems like a decent first step but the functionality.. a Perfect nice 3/2/2 1400 sq pft per side is 575k , this one could be 365k if they accept my offer i sent last night)

The denial was based on the following reason:"The proposed use Visitor Accommodations is prohibited in the RM-1 Zoning district per table 14-602-1".At this juncture, it seems my next step is to appeal to the Zoning Board of Adjustments.

Again, very easy to find... the deal is the challenging part.All the best to you on your journey!

So the alternative would be stepping out of my comfort zone and buying in another market where, theoretically I can get the same returns on an already built property including management fees.

Assuming you do not want to take those steps, I believe investing in something like VTSAX yields better returns and is "safer."