As an example if your house was going to sell in two weeks for full price, and some random person came up to you and said I really want this house but I need six weeks to get you the money.

This is more common for investors who live out of state and can't see the property in person, so they get the property "under contract" and then send a contractor or inspector if their offer gets approved. 

Probably personal preference, but if anyone has a strong opinion, I'd love to hear it! 

You can express your willingness to offer a new lease to the more responsible tenant, but it's important to avoid getting involved in their personal issues.

Even if you ended up renting to another person with some of those features.

Mind if I steal/share it?

In my experience, lots of section 8 recipients have limited access to personal vehicle.

I noticed that you operate in Chicago, any real estate meet up you'd care to share?

If someone is interested I can share info after signing a NDA .

Any insights or advice you could share would be greatly appreciated.