I realize comparing the two is apples and oranges as they are both fundamentally different strategies.

My older Multi Units in the City always have higher maintenance than my single family properties in the suburbs, so its not easy to compare apples to apples in a sense.  

That $50K is now IRA capital for investing, and could be used to purchase a 2nd property, issue a hard money loan, or go buy shares of Apple if you like.  

Trying to get the current landlord to evict the bad apples. 

that's such an apples to oranges comparison those numbers arnt useful.  

Once you find what prices are these properties going for, you could make a decision based on that.Make sure you compare apples to apples i.e., age, square footage, style, rental income, etc. are the same or very close. 

Hey I'm in Chicago area now but from apple Valley and want to start investing there too.

My technical career started with HP and then I moved on to NeXT (today's Apple).

That way you're comparing apples to apples.

So just make sure you compare this options with conventional financing because you can use 5% down with conventional.You can price them apples to apples to make sure you're chosing the right option.Keep in mind if this is your second use VA has a huge 3.30% VA funding tacked on up front.To make it apples to apples you'll have to hike the VA rate up from where it is now (around 3.375% to about 4.00%) to generate enough lender credit to payoff this 3.30%.