Some really put some time into this and considering the various angles. 

Cabins do great in the summer time for this area.

Real estate's "gross rent multiplier" is Wall Street's "sales to revenue",  "cap rate" is roughly "P/E ratio".When evaluating markets and investments I tend to start with GRM (or lazily the 1% rule), then attempt to return a cap rate based on assumptions about costs, then I work my way to multiple years of projections (assumptions about inflation, amortization, tax benefits, etc), and if I am partnering with one of my smart friends I have to pull up an IRR (internal rate of return).I also look at regional employment levels, median income to rent ratio in the zip code etc. 

Glad to have you as a part of this awesome community, Chandler! 

Quote from @Gary Campanaro: I wouldn't consider it unless it were agreed to up front.Cancellations are part of her business, and she needs to accept that.

The lifestyle question is one that you must determine, then narrow down what parts of Chicago provide you with that lifestyle, then we can really answer the question- How is the market doing in those specific neighborhoods?

Dependable routine maintenance is a part of this property with a full time team on site at the villa. 

I am glad you highlighted the management piece as this is a crucial part of buying in another market.Excited that you are stabilized and are generating cash flow on that deal. 

Many times a lender buys a property back at a sheriff's sale/auction where they are selling properties as part of a foreclosure.

Hello! My name is Abriauna. I have been listening to Bigger Pockets podcast for a couple of months now and I am learning so much but still in the beginning stages of learning how to jump in to real estate investing. I...