*****@Alex Franks suggested I clarify my first remarks, so I did with:*****Alex, thanks for your response.To clarify, the goal is (relatively) passive income, to build wealth now with current cash flow going towards purchasing more property or more debt, and then to supplement my income later (10yrs+).

What I have seen is that business lend-worthiness can supplement personal credit scores in larger deals.

As in, I'm 30 now and I'd hope to keep them until at least when I'm 65+ and use the rental income to supplement whatever other retirement income I'd have, or potentially sell them at that time to fund retirement. 

So there's always the option to become a licensed agent, loan officer, or appraiser, all of which would provide supplemental income (perhaps eventually better full-time income) and help you network in real estate.

Went off the advice of a few senior military officers and my old economics professor suggested Brandon Turner's book... which led me to the podcast...which eventually led me here.Long terms goals include financial independence by age 45 and while Real Estate is just a component of the bigger goal, for me, at this point, I would like to maximize my opportunities to buy and hold a few properties that can potentially become streams of passive income to supplement my larger portfolio down the road and have been working for about 4-5 years to put myself in a position to do that. 

No reason to be at the bottom supplementing your tenants rent.

You are correct that the majority of our data is pulled Airbnb listing calendars - we supplement this with real data from 100,000 rentals around the world.

I do not work for deals, I love reading about it but I will take the supplemental income and stability that comes from my 2 multi families.

I am choosing real estate as a form of diversification mainly to supplement my income.

If the contractors estimate is higher, the insurance company may, or may not, supplement the claim.