However, when the property is for investment and Titled in the name of an LLC, for all intent and purposes, its considered "Commercial," even on 1 to 4 units.

John,1 to 4 units are priced via comparables not based on cashflow. 

And I want all of the tax benefits 😀But if I did invest I’d want someone to have owned or led a previous syndication with comparable magnitude.

@Chris MacDonald  I am not a CPA but I am and have been a real estate professional for tax purposes for 40 plus years.. so I write every single trip off.. as I am always looking at new deals.when I was in Thailand last week I met with a condo developer who was offering 7% guaranteed rental returns.. on his condos went on a tour got the brochures and am considering that investment.. so that is a business trip. 

Comparable rents would be 800 month for 3 bed and 600-700 for 2 bed so gross rental income of 3700-3800 fully occupied.

How does it compare to market?

You will have to prove that you have either moved or are moving up in home size compared to the property you already used FHA on.

1) When making these types of decisions, it's important to also compare an alternative.

The prices in Bonita Springs work better compared to Naples however one aspect of Bonita Springs that scares me is the flood insurance.

Miami does have higher rents compared to the other cities I have mentioned due to population density.