Personally, it’s something I always expect from a short-term rental, and it can have a huge impact on your reviews.To make things easier for both you and your guests, consider smart tools like locks, outdoor cameras, and smart thermostats.

I have a situation where a person I know is moving out of the country and would be looking to put their home for sale in the summer.

Yea this is a long-term personal play more than a strict STR deal. 

I personally think being a landlord in Chicago is easy and I have never had an eviction. 

You'll want to put together a personal financial statement (basically lists of all your assets and liabilities) and have your tax returns ready.

Would love feedback from anyone with personal investing and/or property management experience in these cities.

A FHA 203k Loan is where the purchase price and rehab costs are rolled into a single loan.The downside of using FHA or a FHA 203k is you will need to live there, for a minimum of one year (to satisfy FHA Requirements); AND because you closed personally, you will not have Asset Protection, in the form of closing in the name of a LLC.

Account holders can't take any write-offs personally for investments made in the 401k.

They clearly had no intention of paying off the loan in October but sought instead to further reduce their loan balance during a time of the note holder's personal hardship.

This will allow you to remove the person and do the financing on your own.Home Equity Loan/Line of Credit: Since you're looking to access equity, a home equity loan or line of credit (HELOC) can be a good option.