Decided to pull the trigger on the duplex as I should be getting an Cash on Cash ROI of 18% on it.  

Sounds to me like you already decided that you want to flip since your goal is to make quicker money in the short term.

Then I'm trying to decide how much more I should take out on my loan, to reinvest into purchasing an additional property.

I am selling my house, and the buyer has decided to back out of the deal two days before closing.  

So it's best to learn the market and check out a few parks before deciding which ones to work in.

We just closed on the townhouse yesterday and decided in the process to go ahead and open the checking account with the bank. 

How do I decide which avenue is best for me to peruse as a career?

In that case, then you are getting a landlord policy.If you ever decide to do a flip, it would not be a landlord policy, it would then be a vacant property policy...just for future reference.

About a year and half ago he decided at age 30, he wanted to be a GANG-STA, not sure if that is the correct spelling, but you get the idea.

We're probably in about the same boat in terms of experience, but if you decide to go forward with investing in St.