Critique my 5 year plan using VA loans, house hack and wholesales

[Brandon Thomas]

Hello BP community! I am looking for stable financial freedom in the next 5-6 years investing in multi-family properties. I am currently active duty military and I own a single family rental property in Oceanside that has almost $200k in equity and has very negligible cashflow (for now).

My plan: Upon my return from deployment at the end of the year, I intend on using the VA loan to buy a multi-family home in the San Diego or Oceanside area (depending on my next set of orders) and use it to house hack. This property would most likely be in the $1-$1.5 mil price range. By house hacking, I would save on average about $1500/month, yet I will most likely have minor negative cashflow in the first 2 years, but the properties should have high appreciation.

In 2022, I intend on purchasing two multi-family rental properties out of state for the sole purpose of cashflow. They would be in the $200k price range. In order to fund these properties, I intend on focusing my craft on wholesales and building/saving the money for the down payments on the houses. My intention is to find houses that can yield $400-$500 in cashflow each. 

In 2023, I will be ending my services in the military and I intend on using the VA loan one last time (after refinancing the first MFH) to buy another MFH for appreciation and to use as another house hack. In order to ensure stability during eventual crashes in the market, I plan on paying off my 5 properties. I would use my W2, money saved through house hacking, and income generated from wholesales to pay off the principle of the cheapest property in my portfolio. I would then use the increased cashflow from that property to pay off the second cheapest property. I would continue doing this until all properties are paid off. At the end, I should be generating nearly $20k in cashflow and be worth $3mil.

What do you think of this plan? Are there any gaps to my train of thought? Is there a better/faster method in order to accomplish my intent of stable financial freedom? 

As a new investor, I am a sponge to advice and critiques. Thank you for taking the time to read this and I look forward to the responses!

[Joe Splitrock]

@Brandon Thomas you may have heard the saying, "no battle plan survives contact with the enemy". This plan has several ways things can go wrong, so be resilient and able to adapt to a new plan.