Since we don’t know what condition the house was in prior to her moving in, we only specified all the areas requiring cleaning and some large nails/screws in the walls, which she signed.

SmartMove and MyRental give full checks on renters, while Zelle and PayPal are good for getting rent online.

A big issue you might run into is that most lenders will require you to qualify carrying two mortgages in your debt-to-income ratio.

I hereby give you 30 days to vacate or qualify for a new lease with the appropriate business name, license, insurance, security deposit, and other requirements.

The building is located in Berwyn, IL... just outside "Chicago Proper" where STR licensing isn't required.

I've never had to fill out a form online (and as the owner, I might be annoyed if I had to do that-just being honest).They let me know when a lease is coming up for renewal, if someone breaks their lease and once a new tenant is in place.

It sounds like if appreciation is the main goal that will open up different markets for you that will require more capital to gain that appreciation. 

I also got lucky and found a group of people to help me with the eviction, as the sheriff requires a minimum of eight people to do the eviction when it takes place.

One of the requirements is to have a trustee. selecting a friend/family isn’t an option for me.

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