The ultimate goal is to build a sizable rental portfolio to supplement my income and achieve FI by 35. 

You would have to purchase a supplemental liability policy in increase your limit to $300k, then you could qualify for an umbrella. 

I attempted a very similar approach to say "look, im aiming to have this rented out for a third or up to half the year via AirBNB... and want that factored in for liability sake more than anything, not interested in any supplemental loss of rental income" .... she simply replied "Oh, ok, did not know that... good to know, I can up the liability to $1M to cover you in that regard, and add the 'Home Rental' package to it that is $271 annually".

Third, does anyone know of supplemental resources that can help me navigate the audio (i.e.: a digital program, or agenda PDF or other kind of document)?

@Alec Norman One option to consider is to get a SFH and rent out the lower level to supplement your cash flow.

To supplement this question, what if you are partnering with someone who has more capital/resources/expertise/real estate skills than you, what would make them want to partner with me? 

For the most part they are equity investments in high appreciation areas with my salary supplementing monthly operational losses.I am looking to expand my portfolio through additional purchases that cash flow.

If the property does not sell soon after the rehab is complete, we will rent it out so that we have supplemental income to cover the cost of the loans from the hard money lender and the original seller.

You can report that to the insurance co, too, and hopefully get a supplement.  

Hello all,I am a homeowner looking to supplement my income by purchasing a second home, preferably a duplex, and renting it out.