We are a local chicago mortgage banker and have very competitive products to help you with creative financing and also your portfolio of single families as well!

Cash flow projection using 50% rule:1450 - 725 (expenses at 50%) - $739 (mortgage) = ($14).  

$10K is ~25% of your annual income, so combined with the mortgage and car payments, you won't have much borrowing power.Find out if the bank really would lend you money if you sold your current home.

I needed the lease in place to buy (get the mortgage on) a bigger place for my family, and he needed a place for his family. 

Network and connect with a realtor, trusted general contractor, mortgage officer, private money lender, banker, and attorney.

Maybe they’ve only missed 2-3 mortgage payments? 

Do existing mortgages get wiped out?

Go over the mortgage numbers with a fine tooth comb.

You can in fact use the rents to qualify to help get a higher purchase price approved.You are smart to be cautious because it will cost you money to start the mortgage process, pay for an appraisal, inspection etc.

If you refi to a renovation loan by including the ADU costs + paying off the existing mortgage, would your total monthly payment be financially comfortable and agreeable to you?