I was wondering what solutions anyone had if you were in this guy's shoes?

If the person showed up at 1:00 pm, or even 12:00PM, or even 9 AM the day before, they can still catch their train and they are considered ON-TIME.If I were in your shoes, and a "grace period" is not outlined in the lease, too late is 12:01AM on the 2nd, and a late fee is applied.

@Howard Johnston if I was in your shoes, given current interest rates I would either cash out refi (take out a mortgage) or get a HELOC to use the equity from my home to have all the cash on hand.

In my opinion, the Park street, NY St, Dover St (and towards Red's Shoe Barn) is a C class area.  

Her only other negatives that come to mind is she has destroyed several pairs of shoes and books by chewing on them.  

Assuming without evidence you are not married...if I were I in your shoes, I would:1) Figure out where most of your friends are living2) Find a convenient block or subdivision in that area that is mostly owner-occupied homes3) Buy a 3-BR house there with an FHA mortgage and move into it4) Get 2 roommates and collect reasonable rent from them5) Live there for at least two years6) Sell when you get married or have another reason to move (take the tax free gain)

If you were in my shoes, what approach would you take to building your real estate empire?

@Daniel Venhaus in your shoes, I would buy a duplex, tri or 4 plex and house hack.

Any insight from individuals that were in my shoes when starting out would be helpful.

Zachary Sit, As Minh said above, I got tired of the "w2 life," waking up early, wearing suits and ties and shiny shoes, and playing diplomatically with all the execs in the sandbox.