He will have to put more than 3.5% down if he is not occupying.

If you can own the property and pay a similar amount for a similar lifestyle, it's probably a good decision (assuming you can afford it if it doesn't go perfectly, needs repairs, etc.)With house hacking the rule of thumb is: The more uncomfortable you're willing to live, the better the numbers will be.

If its college students/young professionals @Nathan Gesner gave some solid idea.If there are a lot of tenants with young kids, maybe a safe play areaAll depends who lives there

"DO MORE mailers". 

I would allow a payment plan, but I won't spread the payments more than six months.

Depending on the exact location, age, roof construction type, etc, there definitely could be a few things to watch out forAssuming the roof is of a reasonable age, it's still more than possible to cash flow with these properties, even after accounting for recent increases in insurance rates that we've seen.

I'm more of a straight to the point investor and just want to know what the endgame is in the deal so I have more clarity.

The point is to profit by finding a great deal on a property, then passing the deal on to another investor willing to pay more.

As a beginner, I’m still reading and listening to all the great advice and content out there, but tentatively working towards house hacking via a multi family property in Philadelphia.  

You don't give any indication of what you can afford, so it's hard to give you much more advice than that.When asking for directions, it helps to know where you are at and what mode of transportation you are using (foot, bicycle, Ford F-350, Porsche 911, etc.), and where you want to end up.