Also, many people pay some bills late but not their rent because a late credit card payment doesn't cause them to potentially lose where they live.

He doesn't have a website. 

In your case, the agent also wants to lock you into a future sale, but that doesn't incentivize her to place a good tenant.

I agree it doesn't seem like they have my best interests in mind.

Little background on him, he’s 20 yrs old, and doesn’t have much family to support him with this decision.

Because if he makes this loan with no desire to buy the building he doesn’t deserve to lose his money but he should expect to.

@Scott McGadden, It really doesn't provide an advantage to pay the mortgages off before selling. 

If a person doesn't fit into one of the two categories below, what would the point of posting on this website be?

LOC on business purpose doesn't really make sense from a lenders perspective.Think about it, you have to tie up funds and not earn a return until the borrower wants to use them.Time is money and if your lending money you want a return each day your money is out.I'd strongly recommend just going with a cash out refinance and avoid spinning wheels looking for a LOC. 

That should cover any overages that the STR insurance doesn't.