It depends on how deep is your knowledge, your experience, your willingness to invest in automation technology, always having a backup or two, your location in the community around you, of your property is in pristine or run down shape, whether you use the cheapest appliances or make things complicated or not,You didn't mention whether self-managed whether you mean you are on location or remote.

Hey @Beth Anderson, I wouldn't complicate it too much since you are just starting.

The best way to do it is when you actually live on the property, ie. a double/duplex, or just renting rooms in your home.It's an entirely different set of skills from long term rentals, but I disagree that it's significantly more complicated.

If you do decide to invest in Florida, it's a good idea to enlist the services of a reputable property management company to help with tasks such as screening tenants, collecting rent, and property maintenance.It's important to manage risks when investing in out-of-state properties because it can be more complicated and may need local support from property managers, contractors, and real estate agents.

The problem is not only that existing tenants suffer, but that local government will be pressured to pass legislation that will be extreme and engulf well run parks into spending unnecessary expense and complying with rules designed to provide residents with services they don’t want.  

What you are proposing is completely unnecessary. 

Complications:-The condo would not cash flow if rented out.

I obviously gets complicated if the splits are not 50/50.

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. 

Now, I am not sure if the banks I have dealt with have just made it complicated to explain to new comers or I did not understand (after repeatedly trying to understand their process) it completely, but it seems too complicated.