As mortgage rates eventually drop, your cash flow should improve over the long term.

I'm paying very high monthly fees and additional management/service charges but am still not getting the help/education I would like.

To address this, we agreed that I would work in the business for six months to verify the financials, which so far align with his POS system.My main issue is that at 23, I don't have strong financials to get a conventional loan at 75% LTV with a ~7% rate, and the seller's lack of financials complicates bank approval.

Very low fees and probably equal or better rate - I have gotten 80K personal loans from SOFI. 

Pro-rated first month's rent would be due at move in. 

Could have sent Rate increases out prior to using Rent Roll for future revenue stream. 

Most hard money/DSCR lenders don't lend in South Dakota, so I can foresee a low closure rate on deals since financing will be difficult to get.

Yes, in my opinion because of the terms and rates of private money it is best used for short term acquisition and rehab.

The revenue after expenses (including mortgage, taxes, airbnb fees, etc) was significantly higher than with long term renting. 

What is your interest rate?