At the time, my two oldest boys were playing middle school football, so I talked to a handful of dads i was friends with and convinced them to look at this potential investment opportunity.

Just put simply, all cash means no contingencies and in NYC that's the way the game is played.

It would be interesting to play around with and see how fast you can pay it off if you increase by 4%, 5%, etc.  

I suspect that other factors in your financial profile will play into the answer.  

I'm guessing that your insurance company would have an issue with this -- in my experience, when you purchase insurance as a contractor, you can't pick and choose when that insurance is in play.  

There is also a time constraint at play, how long does it take to find a deal and close it then get it rented?

We had a tree company to clear out some old dead trees and vegetation.

vanilla purchase transactions where you aren't exposing the transaction to any reliability risk because it's so simple a dead chihuahua could underwrite it.Just to add confusion to your life, your realtor referring you to someone like me will likely call the local-to-you-me a mortgage broker even though in reality it might be quite rare that the local-to-you-me brokers on REI deals.

I went with the 15yr loan putting down 30% to save on interest and get the loan paid off ASAP, since this is a Buy & Hold play. 

I don't want to try biting off too much at once, but I also wouldn't mind making this a full-time opportunity for myself if it plays out correctly.