Seeking Advice on 10-year Plan w/VA Loan to Start

[Matt Dubois]

When I first started thinking about getting into REI, my initial thoughts were to do live-in flips with the goal of being able to pay cash for my "retirement" house approximately 10 years from now, so I won't have a house payment on my pension. However, after reading, and reading, and reading some more, I'm thinking of changing that goal to not only be able to pay cash for a home, but to also build an income stream through rentals.

My current situation:  Renting a 2bd/1ba apartment in a garden-style apartment complex.  Employed "full-time" but my work schedule affords me a significant number of days off, and I have the skills and capability of doing most renovations myself.  I currently live in York, PA, about 50 miles from work in Baltimore, MD. 

REI PLANS: I will be using a VA-Loan to start, so I will need to occupy the house for 2-years. I'm not planning on making my first purchase for about months so I can pay off some of my current debt and lower my debt-to-income ratio. Although I will be retiring from my "real" job in 10 years, this doesn't necessarily mean I will get out of REI at that time. Plans are to buy distressed properties, whether SFH or 2-4 Units. Mostly likely buying in the Baltimore area and moving out of York.

LIFE PLANS:  Retire from my current job in 10 years.  I will have a pension to live off of, but due to my divorce it won't be enough to live comfortably with a house payment.  I will, however, be changing locations from the Baltimore, MD are to a beach in North or South Carolina.  

Scenario 1:  live-in flips only during my 10 years to be able to pay cash for a beach home when I leave the fire department

Scenario 2: 1st purchase a 2-4 unit, live in one unit and rent the others. After 2 years of occupancy (VA Loan), refinance and take the equity to purchase a SFH live-in flip and rent out the unit I had occupied.

Scenario 3: 1st purchase a 2-4 unit, live in one unit and rent the others. After 2 years of occupancy (VA Loan), refinance and take the equity to purchase another multi-family.

Scenario 4: Purchase a SFH and during my 2-years subdivide it into multiple properties. (I feel this is the least desirable/most expensive way, but may be easier to find properties)