If my business owner bank statements did not gain me an approval, I was going to go the hard money route.

Quote from @Bruce Woodruff: @Jesse Valdez you really need to get out of the landlord business.

Master your mornings, and watch your wholesale business explode. 

But it is my opinion you should try Airbnb, VRBO, booking.com and FlipKey and give it a chance to see if it is adding business.

Jim's bleating about government being involved.

Seems odd as this would be a business expense for my business.  

Converting your condo into an investment property and transferring it into an LLC is a smart move for liability protection.You’re correct that retitling the property involves Chicago’s transfer tax, which can be substantial.

I personally have no connections with anyone who is involved in this niche and I'm wondering how other people have started their journey.

I've been toying with the idea of adding an ISA to my sales business.

Make it part of your business model and focus on scaling vs managing.