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.

If I were in your shoes, I'd suggest asking BP in your area for recommendations, to get everything inspected so you can move forward.  

If you walk into your tax person with a shoe box full of receipts and notes along with bank statements in a sack, you're going to pay for it.

If I were in your shoes I'd tell the seller "I understand you would like x$ however, based on what I do and the number of repairs needed for the property I can offer x$.