All this being said, I want to cover myself as much as possible from this.

The PM is covered by the HOA so that's something I wouldn't have to worry about luckily.

Also adding the LLC as additional insured is not effective, as the policy reads that the additional insured is only covered for the acts of the “named insured.”

While it wouldn’t be a long term solution it would allow you to get started and cover the majority of your monthly mortgage / living expenses.

While I don't do a Schedule E for that property, I do have a rent check that covers the mortgage for the entire duration of the purchase and her stay there.Would that suffice?

This way if it was more time consuming, we charge more, but at the very minimum, a $150 fee will be charged.When factoring the cost, make sure that it covers the minimum time just to make it worth it to someone to do the work. 

I don't have heavy interests in politics, but the Democratic Meeting I attend in my town are proactive in bringing guests that help in the developments of my area.

Just make sure you have enough liability coverage ($1M if possible) to cover any sort of potential issues. 

Solution #5 would be if I could obtain an investment loan that would cover the purchase of the note, which would make me the new lendor, AND a rehab of the property.  

No one agent can cover all that.