Again my goal is to get the houses to supplement my income ASAP with as little debt as possible. 

Missed it, yeah 8 acres is small for a functional vineyard without something else supplementing it.

I am the one securing the financing and facilitating the rehab along with supplementing holding costs.

It was intended as a low paying job to provide supplemental income to someone who wanted a part time job.  

. - it's a lengthy answer.Check out the city's main site that also links to supplemental content: https://www.chicago.gov/city/e...Also, here's a BP thread with some Chicago architects weighing in: https://www.biggerpockets.com/...

I am urging him to buy a short-term rental house hack with a guest cabin or even two floors that can be split so he can supplement his income.

New to the industry and looking to find supplemental tools to help me be efficient and effective.

Assuming the mortgage servicer eventually gets the misplaced principal payment, you will have overpaid the principal of the mortgage when you make the supplemental monthly payments, and the mortgage servicer should return that extra principal to you, without question, when they ultimately close the books.The mortgage servicer will not return the interest portion of your payments, and in fact some additional interest may be due when this is settled, despite your ongoing payments, because the interest is collected in arrears.  

I eventually got my MBA and found that it supplemented the learning I was doing on my own.

The doctor discusses your lifestyle with you and recommends some changes in your routine and your nutrition and suggests some supplements.