The owner is a great guy who is an investor and developer himself who is great to work with if you have your ducks in a row. 

Good stuff up there.With me, especially because I've only accrued about 12 months experience in Chicago where we are buying right now, anytime I cannot identify true, apple-to-apples comparables, I might just pass on the deal altogether.Especially in Chicago where you have several types of homes (bungalows, ranches, cape cods, georgians, etc.), you really cannot comp one with the other unless it's the same style.Here are some general tips when comping homes:Never cross any major highways, and try not to cross any major streets if you can.

This way the IRS will receive the 1099-S and identify the transaction as occurring within the tax-sheltered plan.

Our first goal is to develop enough passive income to replace our own mortgage payments and then see where this takes us from there. 

I would develop a solid criteria for size and product type you are looking for.

- Do you have anyone to help you develop the scope of work for the rehab?

A house that has survived 100 years of neglect has probably got good bones, while modern construction is often all about slapping stuff together as quickly and cheaply as possible in order to maximize profit for the developer.

You have to identify what your goals are and set parameters that get you to that goal.

Honestly I don't see a huge issue with starting your investing career in a different market if you are able to develop sufficient systems.

The neighborhood is going through a massive development phase right now.