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.

@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! 

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

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.

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

Locating, marketing and negotiating the deal, understanding the underwriting, using escrow and title, and all of the basics are used so that it prepares for the more complicated techniques.

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