Factoring in that you have acquired ease of finance through the seller at a very low rate, you have a slam dunk.

In your case, you acquired the property in 9/2013 with the intent to sell to a builder.

Although I do have some investment ideas, I simply need to know if my plans are viable, or whether i'm thinking way over my head.I do plan on purchasing my first home using my VA loan. however, In the distant future I would like to purchase and acquire single family/student rental properties.

Is my assumption wrong that you are speaking of a real estate property you are doing what with, sell or acquire or other?

My long term goal is to flip a few houses per year and use those profits to acquire long term rentals.

(though check with an FHA lender)From FAQ on the HUD website:"To prevent circumvention of the restrictions on FHA-insured mortgages to investors, FHA generally will not insure more than one mortgage for any borrower (transactions in which an existing FHA mortgage is paid off and another FHA mortgage is acquired are acceptable)" (italics added by me)In your case, the refinance you plan on doing will pay off the "existing FHA mortgage", then a new FHA mortgage is acceptable.The caveat.."

Getting ready to have a baby here in less than a month so probably wont be acquiring anything new soon, but hopefully in a year or so we will make another move.  

I live in the south suburbs of Chicago and recently acquired an investor.

I acquired a property last year via foreclosure.

On another deal, I had refinanced after acquiring and paid for lenders title policy when I got the new loan.