It will be done correctly every month and during tax time, you and your partners can easily have to CPA/book keeper issue 1099's and get your taxes filed on time with all the right deductions.

Depending on the class of the property you are looking a few thousands of dollars every time.

I agree that 15% cash on cash returns seems ambitious, but I guess it depends on what their pricing and financing strategies are.

@Meghan McCallum - Are you required to pay a city tax on Airbnb in Chicago? 

Further, he's using an @gmail.com email address—don't get me wrong, I run my RE business through my primary @gmail accounts set up for the LLCs, but as a legitimate tax-paying lending company? 

If the option to purchase isn’t exercised, he can sublet the deal again to another tenant/buyer, possibly with increased rent and purchase price, depending upon the local real estate market. 

If it is light, a dscr purchase would be a great option as it is typically 30 year fixed and around 7% give or take depending on cash flow, credit, and leverage. 

. 🤷   It depends how low, low is. 

I know it varies a lot depending on a variety of factors, but what are you seeing on average?

A cost segregation study is a strategic tax planning tool that separates the assets that have a shorter useful life and can be depreciated over 5, 7 and 15 years from the residential rental property or nonresidential real property that are depreciated over 27.5 and 39 years, respectively.