I want to move onto multi-family properties ASAP.

Do I simply jump in with a rental that would (based on the calculator here) give me a 16.56% CoC ROI and move forward from there?

I had an additional 'tenant' move into one of my section 8 rentals and was not told.

One of the important parts of a good deal is the estimated renovation costs and there are still repairs even with a "turnkey" (move in ready house) - I learned that quickly.  

This sort of property is expected to move slowly but there is demand. 

Currently I have the property under my personal name - I would like to move it to an LLC but from my understanding when I transfer the deed to an LLC I have to pay transfer tax once again?

The low interest rate on the property has been holding me back from refinancing but a great opportunity has come up and I want to move the equity to the new project.

When you say out of state, are you moving to the new state?

About a months rent would be covered by the deposit they wont get back when they move out.

You could just move out and rent the entire property.