I dove deep into the strategy a couple of years ago and there were a few insurmountable obstacles. 

That was pretty insurmountable, all we could do was work to stay afloat as a couple.

While nothing was insurmountable, I can relate to how the situations could prevent other new investors from moving forward.

Do you want to save more to invest in the Bay Area, or take on the added (but not insurmountable) difficulty of investing out of state?

You will not run into any problems which are insurmountable. 

If you want to self-educate, there are an insurmountable number of posts you can find by searching BP, either with the magnifying glass above or through google.You don't need lease agreements between you, the LLC, and the bank.Just keep track of airbnb revenues, rental days, and all expenses. 

I'm sure you aren't but homeowners in foreclosure face near insurmountable pressures and they are ripe for the picking with predatory scams.

My company we've got 1,000's of sub $1,000/mo tenants so the risk would be insurmountable.

Yes being socially disadvantaged can hurt, but it is not insurmountable. 

Written leases should not be an insurmountable obstacle.