@Ellis Moyewe really don't know a lot about this situation since there aren't many details in your post... but i don't think this makes any sense for anyone involved here...if it's a flip that's not selling, refinancing may not solve your problem and allow you to pay back the HML in fulland typically a sub to buyer wants a low interest rate... and if you refinance now you won't be getting a low interest rate, you'll just be getting whatever the market offers.and finally.... the vast majority of loans are NOT assumable. 

., Purchase Price: $475,000 ($197.9/sq. ft.).Estimated Market Value: $402,000 ($168/sq. ft.).Financing Terms: 2% interest rate, with a 9-year balloon.Unit B Income: $2,049/month (Section 8 tenant through November 2025).Unit A Income Potential: Similar rent or higher; Section 8 cap for the area is $3,234/month.Monthly Loan Payment (P+I): $1,386.Cash Flow Breakdown (if both units are rented at $2,049/month):Gross Rent: $4,098/month.Vacancy (10%): $410/month.Operating Expenses (37.3%): $1,376/month.Net Cash Flow: $943/month.Key QuestionsWould you be comfortable paying an 18% premium for financing at 2%, especially in a market where current mortgage rates are closer to 7%?

Now, I'm imaging a scenario when every one of these tenants move out that I'll be paying their entire security deposit + interest even if there are damages beyond normal wear and tear. 

The numbers vary per project, but it helps to get things done on time.

Use a quitclaim or warranty deed to transfer the title, and be prepared to pay Chicago’s transfer tax, calculated at $7.50 per $1,000 of the property’s fair market value.

One thing to note when getting conventional mortgages and spouses.There is a 10 limit per person for conventional financing.You can either do 10 conventional in each person's name which would be 20 mortgages for 2 people or if you do the mortgages jointly, will only allow 10 in total.My thoughts are not to own joint assets until you are both married. 

@Juan PerezCongratulations on paying off your first home and transitioning it into an investment property!

if you can't do that, you're just paying interest and the bank is getting rich, not you.

How do you pay for the tax and insurance?

Can they bypass this requirement if paying in cash?