We are based in NY, mainly looking to invest in the Hudson Valley area.

Also depends on how much capital you can raise, your experience, and what returns your investor base is expecting. 

Debt Service Coverage Ratio (DSCR) loans are a type of commercial real estate loan where the lender evaluates the borrower's ability to repay the loan based on the property's income generated.

He also has no driver's license, but he does have an out of state ID.I get a bad feeling that this could turn out bad for me and feel I can decline him legally based on him not having rental references, but on the other hand I think that maybe I could either offer him a month-to-month lease with a guarantee I don't raise rent for 12 months, or require a double deposit. 

There is a significant difference between a "business" and "self-employed". 

I personally view it as a liability protection issue and base the decision on my costs to have the LLC versus the equity contained within.

We are based on Maui and are looking for SF homes and condos to FF and possibly hold for LTR/MTR.

As you move further in your investing and have many properties, then you can start putting multiple together still based on risk tolerance.

AndFor a $250,000 debt/ LIABILITY…. the cash flow is zero… and you’re still put $ 20,000And the Gurus are selling these as a way to make money in 10 years when they appreciate.SOMEBODY BUILD A REAL DEAL BASED ON TODAYS NUMBERS… Use all of the tools available.And build a REAL DEAL THAT SHOWS STRONG CASH FLOW WITH ZERO OUT OF POCKET ( or build what you can)I realize that I jumped in with both feet….

Pay the bill yourself, then reimburse yourself by charging the tenants based on a formula.