If they have not paid by close of business on the 4th, they get hit with a late fee and have to pay with a money order so I know the funds are guaranteed.Second, the tenant is offering to pay rent but playing games.

I have been trying to break into the investment game for quite a while now and I truly feel that it's now or never.

My name is Justin and I am slowly trying to get back in the game.

My questions are these: Should I be worried about the potential for me buying this and zoning enforcement coming after me if I rented it out to two households? 

In the suburbs, you will actually have a code enforcement inspector come out to your rental to inspect (typically when tenants change, but some do it annually even when tenants have not changed), and you will be required to get a heater certification certificate to present to the inspector.

I say ok, I think I can come up with say 10K to get "skin in the game" which should cover the 4 points easily on the type of deal I am looking at.

Do what you know and enjoy, getting creative doesn't necessarily make you more money, it likely means you are taking on more risk and playing a game you aren't prepared for.Everyone's goal in real estate is to create a machine, where in, you stick $1 in the front and it spits $1.20 out the back. 

It's an important and unique identifier for that person and you may need it if the tenancy ever goes bad and you have to collect/enforce a judgment against the tenant. - "No need to ensure proper safeguarding of SSN". 

Usually it's a case of beer, or tickets to a Cardinals game, but never cash.

I like your game plan Matt!