Then i wondered if i even wanted to go with one for my first couple of properties until i scale up to where i might really need it and might have more negotiation with a portfolio of 5-7 properties.

I see that there's absolutely no time to ponder in this game! 

Like i said, I’ve never personally had a property insurance claim and now nearly my entire portfolio is a claim.

If you do enough deals and NEVER play games you should be able to get to the point where you can call someone at the title company and say "I need you to open title on 123 Jones in McKinney.  

There are very, very, very few investors who start at a young age and make it in this game, and this is why.

I've only been in the game since the last downturn in my market, so I can't give a specific anecdote.

A cobbled together option I can imagine for you (and one I've used for myself) if you're wanting to exit the game would be to 1.

CAREIA is a non-profit organization in the suburbs, but they have a lot events: Meeting with speaker, Networking, and Cashflow game.  

I've had a few discussions about the best way to create a plan in order to "snow ball" your way to owning many REI properties (buy and hold for rent).After Googling around and even reading blogs on this site, I've thought about doing something like the following:Buy my first rental property (SFH) with cash (around $60-70k) where I'd expect about $500 cashflow per monthCurrently I have about $105-110k available (after taking out an emergency fund)Then shortly after, buy my second rental property (SFH) but take out a mortgage and put down around 25% on a $60-70k houseThe cash flow on this property specifically would likely break even (at or near 0) but this would be on a 15 year mortgage and I can use some (or most) of the cash flow from the first to help pay down that mortgage faster, along with my corporate job monthly savings tooI feel I could pay it off anywhere from 5 - 10 years depending on the exact strategy If/When I get the 2nd one, then shortly after that, try and get a 3rd SFH rental property and continue this snow ball effect to build up by rental portfolioObviously this is easier said than done, along with risks and I honestly do not have any real experience with rental properties as this is my first time diving into this type of investing.My main questions would be -- Has anyone done a similar strategy to help build their portfolio quicker?

I have a few friends out here in Oregon who have large patches of land normally 2-5 acres I'm not sure if it's high or not, not my ball game but they are getting roughly 10% of profit but bear in mind that's water rights which in Oregon you must have for large scale grow.