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?

Section 8 may call it a BR if it is over a certain Sq Footage and has a closet and then your approved rents go up. 

If the seller requires a balloon payment in 3-5 years, then can I  refinance once again the entire amount into a 30 year loan at the end of the balloon period? 

Then you can focus on your property manager's methods.My property managers do an inspection within 24 hours of the tenant leaving.

If you plan to stay there a long time 10+ years then likely the value will be the same or likely greater even if prices soften in between.

Once we know this, we can then explore options!

@Chris Rogers higher interest rates have caused most Class A property purchases to NOT cashflow for an approximate 3-5 years.So, many naive investors are chasing Class B, C & D properties to cashflow, WITHOUT fully understanding the scope of the additional risks involved:(Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.So, when investing in areas they don’t really know, investors should research the different property Class submarkets.

And if they are 50-70% leveraged, AND the equity is performing at 5-7%, then most people would be living off of most of that come and have only about 10% of it to donate or sacrifice.

If unit needs work to get to market rent and tenant decides to leave then do whatever cosmetic work needed and get new tenant.

If they counter, I would then request info to be able to qualify them as a tenant.