If you have this debt and need money, you may not be preparing yourself for the challenges of being a landlord.

You could structure the deal as an installment sale or a lease option so the property owner doesn't see a large capital gain tax payment for the sale.And good on you for helping out!

Quote from @Noah Wright: Absolutely, happy to help --Thanks!

Find out what financial problem you are trying to solve in the short term until your able to get to more "long term" problems that real estate helps with 

Opinions vary widely on this subject, but consider getting a real estate license.

May I kindly request your help should you have a model I can use?

Here in Chicago, you should expect a range from $200-$275/SF, depending on the location, experience, labor, and material finish level.Are you in a position where you already own some land, or what is your current situation?

Quote from @John Warren: @Delroy Watson I would check to see if you can do this the "right" way and make it an ADU.

Between working around the renovation materials to the 35 minute commute to the first two units I’m having serious second thoughts about this.

What's even more frustrating than asking the IRS help desk, is asking a Turbo Tax "Tax Specialist".