If you're able to work one transaction per year, the commission from that transaction should more than cover the cost of maintaining your license.As others have mentioned, it's totally dependent on your goals and comfort level.

He also owned a floor covering business doing custom tile and wood work all while managing his properties for 50 years.

Hello, I am new and I have been doing my research, it is all still new to me, so I have a lot to learn yet, but my plan is to wholesale houses until I can build enough capital to cover down payments, holding costs, rehabs etc on investment properties.

For example, if you look at recession statistics, generally office suffered higher vacancies and higher rental drops than multi family.

Title company tax certificates will cover all the bases.

The rent doesn’t cover all the fixed monthly mortgage costs, PITI, but

@Jay Hinrichs, exactly, it's far more likely the judgment will be required to be paid, so far more the suffering party, the prior landlord will get paid in the future instead of lenders (i.e. some portfolio &  private lenders) who may not make it a requirement to fund the loan.No matter what, its like attaching a Low Jack that flashes like a Neon Sign when someone pulls a report that says..."

But if they do you are covered.  

When he left, I remember hearing and reading about how much the local economy suffered in Cleveland.

Your plan may cover all of the strategies you touched on, but over a longer period of time with definite transition points.