So to help cover expenses and see some cash flow would focus on multi-unit property. 

I want to start investing in Dunmore, PA.  Any advice is greatly appreciated.  Looking for advice on good areas and areas to stay away from.  Thank You in advance.

If this is how a cash out refinance works, it feels like the strategy is to either have more to rent out within the property (multi-family), wait for average rents in market to increase, rehab the property more and increase rent more, pay off the property/ more of the mortgage and refinance again without a cash out to decrease the mortgage (I don't even know if I can refinance a property twice)? 

I have been looking at both multi unit in some suburbs Aurora/Oswego/Bolingbrook but most those areas.

Meaning the folks sitting at sub 25%, probably 20% DTI with cash still on hand to buy properties but choose to leverage.

Or you might choose to hire a handyman to do some work and manage them more closely than you would a more proficient contractor.

But usually for a tenant occupied it's like $90-120 per monthI've noticed a lot of multi-family buildings are pre-WWII housing inventory - are there restrictions or issues common with that (historic districts, crazy high utility costs, etc)?

First of all, a multi-year lease should be a hard "no" even if it was a perfect tenant.

Don't feel the need rush the process and choose the first one that comes through.

I've read a few of the BP books written by Brandon & David Greene and they say something similar to choosing a PMC.