I feel like I may need to do those roll overs more than couple of time per my life time.

@Max Murphy - Instead of a loan from family, maybe you can do the math and entice your parents to invest with you -- even if it's 75 percent (them) and 25 percent (you).

Right now I would not recommend chicago area at all I’m no professional but as a life time resident of Illinois I can tell you right now is not a good time to be buying property there new taxes are coming out very soon on property, gas , cigarettes and many other things that are going to be having people run even faster the they already are.

It will be a higher percent for a $50K home than a $500K home. 

I have 22 yrs left on a 30yr mortgage and owe 85000 , at a 4 percent fixed rate.

Paint should have a normal lifetime of a few years (we say 3), so you can charge them a prorated amount depending on how long they lived there.

Typically the amount of inflation, say 2 or 3 percent.

In one town near me property taxes are a full percent of assessed value higher than other towns, even in the same county.

I was just trying to figure out ways to get my next property with out having to put down 20-25 percent down because i low on my own funds right now.

There is a funding fee that comes with using a VA loan, but I'm not sure what percent it is.