Too many people involved to do a relatively simple transaction.

We're planning to moved forward with the purchase and appreciate all the feedback and suggestions. 

The only thing a tenant does it prove the rent you can collect as opposed to a proforma of suggested rent.

I would suggest you talk to a mortgage broker or a bank though - if those homes are zoned commercial you will probably have a hard time getting an FHA or low down Conventional mortgage.

Also anonymity today is a joke, I can find out within 3 minutes and a simple $1 skiptrace who owns a property and where they live.

My biggest piece of advice is to connect with local chicago real estate investors in person...highly suggest checking out the christmas party on 12/12:  https://www.biggerpockets.com/forums/521/topics/1218823-chic...

Stick with a simple camera set up outside if you would like.  

That’ll give you flexibility to automate and integrate workflows as your needs evolve.A direct booking site is a nice-to-have down the line if you want to save on platform fees and build a brand, but starting with platforms like Furnished Finder or VRBO is a solid way to keep things simple while you’re getting started.Good luck—sounds like you’re on the right track!

Sometimes back of the envelope underwriting is ok, but not enough information is available here to suggest this is a $520k-$580k opportunity.  

Looking for suggestions on a white paint color to go with the dark wood trim.