I love the 3 options approach. if you connect with me and send a request, I'll share my version.

The vast majority of guests will send me their email address, in response to this request, but it isn't 100% of the guests and it frequently doesn't happen until shortly before their checkin date.If you want 100% of your STR guests to sign an agreement before checkin, you will need to require their email and digital signature before you approve their booking.

Responding to your colleague request now.

You can contact Chicago Housing Authority (CHA) assuming that is who the section 8 voucher is for and request a rent increase.We recently did this with one of our properties and were able to raise the rent from $956 to $1249. 

I have 3 SFH rentals and I personally inspect any repair requests before contacting someone to fix.

I just sent you PM request

If you need that paperwork, let me know by sending me a connection request and messaging me your email. 3.

If the tenant wants something updated, I point them to that clause and politely decline their request.

Also just request the ability to get in for showings, etc in exchange for breaking the lease. 

Per your request:1.