I’m looking forward to learning from your experiences and sharing any insights I’ve picked up along the way!

Where you pick will depend on your goals for cash flow and your budget to buy.

Hey Hey @Veronica Mitchell - The most simple advice is to follow the CTA trainlines.I personally love the South East Corridor of Chicago which has Bronzesville, Kenwood, Washington Park, Hyde Park, Woodlawn, and South Shore.That area will continue to be gentrified because you have the lakefront and CTA trains.Others mentioned NW along the Blue and West along the Pink, Green, and Blue lines.

It usually means there are problems to be solved for the seller which will translate to opportunities for you.Keep it simple on your first 2 deals to minimize your risk.All the best.

@Chris Hains  all in price , vs what you are expecting to sell it for , KEEP IT SIMPLE.

We will shop for used appliances where we can when we need one… or pick up used cabinets if we can, or search eBay for something smaller,  but going to the extreme of personally shipping something big in internationally for one-off renovation needs seems like a stretch of reasonable.Just like you mention, the number of unknowns would not seem to be worth it to me.Just my 2 cents.Randy  

So - somewhere 2 hours away, or somewhere you like to vacation in, or where all your family lives, or where you plan to move someday.Too many people are trying to do exactly what you're doing - pick a market based on a formula - and they end up buying a random 'cheap' property thousands of miles away, turn it over to people they've never met or even spoken to, and then... lose money.  

A couple problems dividing a property and selling in a “Timely” manner and then picking exchange properties of equal or greater value than the lots you sale.  

You picked a great community to join.. have you checked out local comps to gauge the market vibe yet?

I'll figure that out after I pick a strategy.