If you're going the umbrella insurance route, perhaps see if it will cover you for several things including just the routine slip and fall (like mold or earthquake).

If not, you may need to explore the private money route like you're thinking.As for the second question, it can be tough to get a rate and term refi when there’s a second position on the house. 

If I go the conventional route ,at the pace of my savings, I would be able to afford a property in that price range a little over a year later.

I have tried going through the conventional route of HELOC and Home Equity Loan for my primary residence.

But you do not need to go the refinance route as long as your current lender will allow you to do a quitclaim deed to an LLC. 

I recently was at BPCON and ran into a developer and they recommened I take a different route. 

As with any investment PML does carry risk, so investors must weigh their own personal goals and risk appetites against the returns.Long term (after that career of investing you mentioned) I see myself going more heavily into the PML/ LP route.

I have a property in Jackson Michigan under seller financing it was my first time taking this route.

The route David mentioned will work for now, but snowshoeing is frowned upon by carriers and will eventually (sooner rather than later) die as a marketing tactic.

Even partnerships of the closest friends can fall apart, but putting that much trust in a stranger you've only met over the phone or maybe in person a couple times would not be a route I'd go.