This question and the answer can be complicated without knowing your long term goals and investment strategies.You should develop a plan identifying all your goals and what investment vehicles you will use then it would provide you the answers to needs. 

Somewhere around 5+ units is when I would expect to need property management so we can focus our real estate time on new deals!

@Patrick PhilipYou're going to need to conduct a Comparative Market Analysis.

Getting to the point that you are earning 200-250k a year in real estate is probably going to either take a lot of your time to create and manage, or you are going to need a lot invested (like 1-3 million) in order to get that income level.

The places that knock my socks off get steller reviews with lots of exclamation marks and a very excited tone. 

However, you're going to need significant cash reserves to go the first several months without getting paid and I would recommend staying in the military reserves for the sake of health insurance. 

You are going to need to work the phones on this one.

@Art Maydan I agree with samantha, I think you really are going to need to wait until he completely vacates and clean up and bomb the place.

And I do like to flex my imagination muscle and practice my business planning skills.   

I'm going to be starting from scratch once there so I'm going to need a lawyer, wholesalers, contractors, a punch-out guy, title company, etc., and of course fell investors.