While patching a roof on one of my houses there this week, I was delayed by trucks driving slowly through 'driving for dollars'. 

BTW I'm also the VP of a pretty big roofing company down here, so let me know if I can be of assistance,  I have a lot of connections in the contracting world.

I am currently working full-time in healthcare and am pursuing to cover all my families living expenses with our rental portfolio (lean FI) and that timeline would be pushed back if this scenario where to take place. 

Nicer winters, easier on your roofs.

I would even do 6 or 12 month rentals to give yourself room to reevaluated the market and increase the rent.I would then draw on the HELOC which your tenant will cover from your premium rent.I would use the HELOC as leverage as a down payment to a large multi-unit. 

Seller financing: I like the idea of cover to a seller with multiple offers but I’m struggling to develop a 3-offer system.

Looks like you've covered all the numbers pretty well. 

The property I close on this month will continue to cash flow with the fees charged by the property management company.2) Should I obtain a LLC or just have an umbrella policy to cover my assets if something were to happen on my rental property?

However, for someone who is confident they can sell above the breakeven point to cover those fees (which would be about $500k in volume annually in a region with average home prices of $100-120k), the income potential is much greater with the 95/5 split.

Make sure to cover these scenarios in the offering documents.- It’s better to start with a small fund and have it sell out than to start a huge fund that doesn’t fill up, Just better for our track record and marketing.