It sounds like you have a solid, strategic approach, especially with a focus on value-add properties in appreciating markets.

In a handful of years you've got a few properties, and you're on your way. 

Access to Cash Value: A properly structured permanent life insurance policy (like an IUL or whole life) can build cash value that you can borrow against for property acquisitions, renovations, or even as a safety net during market downturns. 2.

After 8 years or so, you've got three or four properties and the world opens up to you at that point. 

I am open to trying what you do with the higher price on one of my properties just to test it.

My ultimate goal is to live in it until I can buy a second property and then backfill my first property with a tenant.

Quote from @Brian Clark: Looking to network in Southern Maine to learn and share about long term rental properties. 

BTW: most owners that have hired a PMC, don't want to speak with you, much less meet with you in person to hear a hyped-up sales pitch.Also, you want to do rental arbitrage - so, you will need to be properly licensed to manage properties you do not own as required by your state & local laws.- why would an owner want to do business with someone NOT properly licensed?

We only look at the income the property is generating for those. 

You are 18, you shouldn't be ready to buy a property yet.