I am finding conflicting information about whether or not this is allowed in Jacksonville, Florida.I've found info stating that the owner must live in one unit and rent the other, or must rent both units to the same tenant, and the two units cannot be rented separately to two different tenants.

@Aaron S.Seriously, I would make and have made suboptimal financial decisions for happiness; everybody has a different philosophy that's mine.  

You want to ensure that your lender is doing their upfront due diligence on the deal, has programs to get the deal done if the final numbers come in different(low DSCR requirements, favorable rent guidelines, etc), and is offering you excellent customer service.

As an example in a different real estate “product”, we owned a 70 unit motel that we had converted to mostly low income housing.  

Currently looking at 2-3 $50-60k sfr properties all being sold by different sellers. 

@Noel Dixon The most overlooked thing I see when people talk about assumable mortgages is that, if you can get approved by the lender holding the mortgage, you will need to bring the difference between the loan and purchase price in cash.

The difference is you have the risk concentrated on a very small sample size.

There are IRS tests determining who is a 1099 vs W2 and then you have your state specific Department of Workers Comp that will have their own definitions of who is an employee and when you would be required to carry Work Comp insurance.To complicate matters there are a few states where the State itself maintains a monopoly on providing Work Comp insurance and the state is the only place to buy work comp (my state is one of those so I can't even sell myself work comp insurance if I wanted to).Here is an article on the three different methodologies the IRS may use to classify someone as W2 vs 1099.https://www.everee.com/blog/irs-independent-contractor-test/If you are really in doubt call your state's work comp office and ask who they define as an employee. 

Difference is Primary you must work remote for a company or have a contract set up to show you will be working in that state.

I'm getting started in the real estate investing world and am almost ready to buy my first rental.I’m debating between two different investment strategies and would love to hear advice from experienced investors here.Would you a) buy a two unit and house hack with 5% down (all cash in around 40k) in an appreciating area with a little bit of cash flow every month or b) start BRRRR strategy right away out-of-state in a C neighborhood.And a third option, if you have the ability to do both concurrently, which one would you start with first?