There are streets on the east side that literally look like war zones--extreme poverty, entire blocks abandoned and taken over by homeless and animals, etc.That being said, that apartment is pretty close to the "Waterloo Arts District" which is a pretty trendy neighborhood that I could see further gentrifying quite a bit in the near future.  

Given that this property is so cheap I fear it would eat up a very large % of the sale price.

Each one of the 3 types of properties you named are a very different animal from the other 2.

But in a reverse, the Intermediary takes title to the new property as what is called the Exchange Accommodating Title Holder (EAT).  

If your thoughts are to break the current mortgage, you will have a penalty to pay out on top of the mortgage balance which will eat a little or a lot into the capital you pull out (depending on the terms of your present financing).For a residential property, when you do refinance, the lender is going to look at you in pretty much the same manner as when you applied for the initial financing.  

I just dont want that PMI and higher monthly payments to eat in on my cashflow for life. haha

The same reason some people don't eat pork, or beef.

If not, I see the maintenance eating up any profit you might make and maybe more. 

How do I know and do I just eat up all these costs?

How do I know and do I just eat up all these costs?