@Jordyn Ohsnot enough info to helpbut if you're using a HELOC for the down payment AND getting a loan, then you're probably negative cash flow given that's 100% leveragei would never do that unless i were going to refinance in the short term

@James Tobin  house hacking is a GREAT way to start.

We then purchased 2 houses for investment purposes.

The investor if they slip and the lender if they need to take the house back.  

Good Morning,So I have always dreamed of getting a duplex as my first house and to house hack to get my foot in the door in real estate investing.

House Hacking using the VA loan to live on one side while renting the other is great.2.

My duplex - built 1989, 2,060 sf, 2 bed/bath, 1 year old roof, value if I subdivide (county already approved) and sell each separately $150k each ($300k total)Investor duplex - built 1995, 2,300 sf, 2 bed/bath, 5 year old roof, value around $310kThe investors initial request was for an equal trade and they would pay realtor fees, which I replied wouldn't be equal due to buying/selling costs (recording fees, title insurance, closing fee, survey, inspections, loan fees, 1031 fees, accountant fees, repairs), taxes would increase due to new sale price, I'd trade a 3.75% mortgage for a higher one, and I'm on the 10th year of a 30 year loan so resetting that to a new loan would restart amortization and pay more towards interest.

I have a contract on a house in Phoenix AZ with a value of $500,000 and a mortgage of $288,000 to be taken subto.

Sounds like the house is not local to you, OP.

My initial idea was to find a house in the &150k-$200k range and flip it for $300k-&350k.