They just cost me a deal, and they are extremely unprofessional and unorganized, I'm not sure. how they are in business.

FlooringScope of Work:Replace carpet in bedrooms with engineered hardwoodRefinish existing hardwood floors in common areasInstall durable tile in wet areas (bathrooms, laundry room)Estimated Cost: $20,0004.

Chicagoland is extremely tenant friendly so understand that going in. 

We were extremely hard pressed to find a painter to do this which is why I said I could do it.

Do you have any books or resources out there that he can dive into to help him hopefully avoids some of the common pitfalls?

I also advertise before someone moves out to get a new tenant before the current one leaves. 100% occupancy on a LTR is very common for me.No idea on a MTR.

Btw, this kind of note-taking has been extremely helpful in other aspects of my life, and I imagine it will work quite well for real estate as well. 

You are correct, it is common for DSCR lenders to require the borrower to be a business entity in Florida, and some other states sprinkled across the US.

My experience in the last 15 years is that except in the most extreme circumstances, an investor is going to need some of their own capital to make a deal fly.

@Jason Sung Yes, this is common.