The exposure to the area you want to dive into is invaluable.  

Good afternoon, AndrewThank you for your kind message.When we took over the house we had a tenant at the 1 bedroom(with extra bonus room in the attic)apt for which we decided to not increase the rent at least for the first year, that tenant pays $1150, my second tenant is an elderly couple with section 8 both tenants pay all utilities separately, we are only responsible for water and landscaping and common area lights.

Seeing all the taxes and even crazy amounts more on my bonus kills me.

Most likely with a bonus. 

In my opinion, with your strong analytical background (as well as a stable job w/ base and bonuses I'm assuming), I don't feel you'll need to do any 'grunt work' for a more experienced investor to get your foot in the door.

If you do go for cashflow, just make sure you understand the risks that come with Class B and C properties. 5) BONUS - @William Spekhardt while not wrong with his note about HELOC's and rates, was not 100% correct.

Did you know that you can use bonus/secondary entitlement to use your VA loan again without refinancing or selling your current property? 

The unfortunate thing here is that investment properties foreclose at a higher rate than primary homes so many banks just don't want the exposure to this.

The goal here should be to expand your exposure/holdings.

@Tyler Brown, two key metrics I always employ in addition are the risk of cap ex exposure and volatility of the geographical market.Going from cap ex risk to something newer might be a good idea.