I am looking for a 8-10% return after I move out and rent out both units.

Here's a legal article that explains what your involvement is and what the process may look like: https://www.paletzlaw.com/2020/01/28/tenants-and-bankruptcy-...

Moving between assistance programs usually takes about 45 days.

So he does not plan on moving out anymore and will stay until the remainder of his lease.

After the tenant’s year lease is up, I plan to move out and rent the entire building.

I have a 3 flat in Lincoln Park, Chicago, IL that I am planning to list for sale in the next 3-6 months.Currently owner occupied in 1 unit (Duplex up, 3 bed 3 bath).The other 2 units (2 bed 1 bath each) are rented.I am wondering if it is more attractive to buyers to leave the 3 bed 3 bath unit vacant when I move out, or should I place a tenant in there and then list for sale?

It has to be presented through your attorney (or by you, if you have the knowledge of the process).You lender on the auto has a say as to whether you keep the car.

I don't recall why we didn't move forward; I think the operator wanted more than we deemed it was worth.

Due to item 1, adding an ADU can require years to start achieving any return (once the accumulated cash flow recovers the initial negative position).4) Adding an ADU is a slow process.

You can't count on believing that the family member will not produce a handwritten lease (real or not), or other paperwork & tactics, to throw a big old wrench in your initial/expected timeline.You CAN expect that if they see you as the big old rich/developer/bad guy enemy, they will do as much damage as they can, and drag their feet as long as possible.See if you can feel out what the relative actually wants/ needs, connect/come prepared with info on resources for local "housing help" options, etc (perhaps), and figure out what you can do to solve the problem (cash for keys with an incentive for quicker move out timeframe?