You could sell the 50 units and buy say10 properties-airbnb maybe-and have that supplement your gains from the sale.

I've kicked around the idea of diversifying into short-term rentals (not switching, just adding one or a small handful of properties over time to supplement my regular portfolio). 

Plenty of investors have supplemented their rehabs using credit cards and end up fine at the end of the day..

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.