Buy a property for $75K, spend $25K in rehab, then sell for $135K. 

If I intend to spend/use that money in the next year or three I put it in the bank. 2.

I'm probably overthinking this, but I'd rather invest in the right strategy now rather than reworking and/or spending more down the road.And in the case of this newest rental, it will need new locks for the front door, side door and garage service door.I guess I'm not keen on having multiple keys for the same property so mixing and matching the schlage with landlordlocks won't work.  

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!).

All PM's carry E&O insurance to protect you.

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.

Try reaching out to @Edward Schenkel about how you can structure it to protect everyone's interests.

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. 

The neighbor was understandably upset so I’m going to wait for him to let me know the damage.I was looking through my policy and I’m not sure which line item covers the water damage to my neighbors apartment.Building property protection.Personal property protection.