Depending on your situation you can get more then one VA loan, and even maintain more then one VA loan so long as you stay below the hard cap.

My VRBO is on a lake close to a University it stays rented.

He talks about starting with a sick or vacation day, and telling your boss that you couldn't stay away from the work you had to do, so your worked at home and found it to be so much more productive because there are less interruptions and could focus more and got more done.

A lot of people are nervous about getting a deal done and stay idle.

I'm trying to stay a few steps ahead so I can put a long term game plan together. 

Seems like this guy has a good thing going, just didn't adapt with technology though at all. 

Are you thinking of staying in the South Side with your investments or go somewhere else in city?

You may get tenants that stay for years .

I am looking for long term tenants which could possibly stay 2 to 3 years but the initial lease will be one year to begin with.

If anything it constitutes an intent to stay another month.The easiest way to handle it is to ask the landlord for a month-to-month while you move out, with an agreement that you'll vacate within 2 weeks of the landlord finding a new tenant.