The issue I have been running into is everything on the market is being pursued so aggressively that everything I have looked at getting and is a decent deal, ends up getting bid up past what they are even asking to the point there is hardly any margin to work with.

In the long run, what's $280 a month if you're buying properties right.

Id much rather be mixing it up in a BJJ or Muay Thai class then logging miles running.

Buying just a house every year or two over the long run will make a big difference in your finances at retirement.

I, too, am running into similar issues. 

The problem that we are running into is funding the renovations.

Both have cheaper and smaller versions that can be bought in the 40-50K range, and both have homes that run 200-300K.

Continue with a lawyer and let it run it's course.

If you have any real estate friends (anyone who works in real estate) ask them to call a title company they have a relationship with and get a list of these properties - they can run it for you.

@Zach SchnoebelenSince you mention train ride, I think of the South Shore Line which runs from the Loop all the way to South Bend IN.