Nice current apartment to crappy VA Loan Rental

So I can't help but ask this question? So I live in a really nice apartment in the Wicker Park area in Chicago. I love the bldg. I've lived in two different units but I want to get into the multifamily game. At my price point (300K) I feel like I might have take out additional life insurance and all that money I was gonna make would be tied in insurance premiums? Worth it? 

Plus I'll have the worry of having to get a car since I will no longer have access to the "L" (blue line) 

So the feeling of not being in a nice area, added expense of a car (which I'll have to incur regardless)

Thoughts?