That way you theoretically offer a better option for someone looking to do exactly what you did (live in one unit, rent the other one out). 

The great thing is its on the counter offer and the buyers agent has to explain why the buyer should pay more than what the seller is offering.

@Sebastian Tamburro you're going to get advice/offers from numerous people trying to profit off you - be careful!

So with the full fee we counter offered and that busted the buyers budget so they could not get the really cool upgrades the wife wanted..

I first contacted occupants and offered cash for keys.

I have a friend who is further along on the path (has done 5-6 of her own) who has offered to help as a consultant of sorts.

Hey @Matthew Giblin - I'd have to echo @Shamar Gregg, Chicago offers a great section 8 program through the Chicago Housing Authority (CHA). 

But I can't help but think that I could benefit from the occasional discussion about real estate strategies or bounce opportunities off one another.Coach Carson's RPM program details below:Cost: ~$2500/yearBenefits (form Website):Personalized Coaching: Members receive direct support and feedback from Coach Carson and selected coaches, including monthly group coaching sessions, one-on-one "hot seat" calls, and small group coaching within Action Teams.Action Teams: These are accountability groups of 8-10 members that meet weekly over a three-month period to set and achieve goals, fostering perseverance and resilience among participants.Comprehensive Resources: Members have access to a repository of documents, systems, checklists, and more in the community swipe file, including tenant screening criteria, due diligence checklists, and rental analysis spreadsheets.Exclusive Community: RPM offers a private community of like-minded investors who prioritize time and freedom over scaling rapidly, providing a supportive environment for shared learning and growth.The Group Targets:Investors with experience owning 1 to 8+ properties, whether short-term (e.g., Airbnb), mid-term, or long-term rentals.Individuals who are coachable, hardworking, and value time and freedom over aggressive scaling.

I noticed I had several with Chase, unfortunately they discontinued their HELOC offerings since COVID...

SF's market is still very nuanced and strong due to the low inventory and demand here, homes still going above ask with multiple offers.