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. 

@Timothy Swaan My plan isn't overly complicated, but I think where most people fall short is simply not CONSISTENTLY following their plan year after year! 

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.

And some people are just not made for this business, we see them on here every day...this is a complicated business with lots of moving parts.

Those types of offers are complicated and probably honestly not even worth their time to write up. 

To make things a bit more complicated, his exwife was never removed from the lease.

I keep comparing to Aussie and other countries world wide.Buyers agents pretty much don't exist and only listing agents do.true, US is almost always the most complicated one, in other country no need to have buyer agent but there're more, no need to pay tax when selling house, no need to put all 2000 pages disclosure when selling house  , no need to have house with so many certification (required in some states ) before renting it out , no need to hire expensive licensed american-born General contractor when repair house, no need to call specialized licensed educated electrician / plumbing with ipod because it's just .... plumbing. no need to pay tax with annual increase .... no need to pay ridicilous amount of insurance every year no need to check their credit score and immigration status when renter is impying LOL the list is on and on

It's about to get a lot more complicated and I suspect they couldn't answer any specific questions right now as everything is in flux.

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.

This gets complicated and is not a DIY project.And, depending on the specifics, various other limitations can come into play.