One I bought from a neighbor , one from a drive by while doing service calls , one from a customer , and one from a friends mother after she went to assisted living . 

By the sounds of it, you intend on spending a reasonable amount of time in the state, and so your personal enjoyment of the place is as equal a priority as the investment side.If you think you will be travelling back to Chicago a lot during your time out here, then a front range/summit county location like Jon has suggested might be in your best interest, so you arn't too far from DIA.If, however, your goal is to get far away from the highway, then come and visit us in Telluride! 

Right now my credit report looks like I love spending, but divorcing a narcissist cost me about $40k and $582/mo in child support, otherwise I'm incredibly frugal (cheap!).

Happy to assist and network

Good luck and let me know if I can be of assistance.

Do you use a virtual assistant for your wholesaling or flipping business?

The elderly woman is now in assisted living, so two properties are involved.

So I already spend a lot of time studying cities and their history, touring neighborhoods, analyzing how they've developed and progressed, and all that jazz.

I had wanted to do something I could be more proud of.Second mistake was a failure on my part to have an understanding with my partner/contractor as to how much time he would be spending on the project, as he had other outside work. 

Let me start by saying I’m not a cpa so this isn’t tax advice, go consult a cpa.From my understanding if your AGI is above 100k they start phasing out how many losses you can take (capped at 25k if you make under 100k), once you hit 150k then you can’t take any losses.The only way (I’ve seen) around this (assuming you’re married and you file jointly) is to have one of you be a “real estate professional” which means you spend 750 hours a year working actively on real estate and that you don’t spend more time than that on any other job.If you meet that criteria you can take unlimited losses and use that to offset other income, so in theory you could make say 300k and show losses of 350k and pay zero income tax.