Lower payments increase cashflow and enable you to invest more (in RE, equities, etc). 

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".

Technology has enabled communication with a remote CPA through phone calls, emails, skype etc.

There are online services that enable you to search for more detailed contact information, but those cost money and are usually designed to create mailing lists for a large number of properties that meet your search criteria.

We felt Zillow's Rent Manager had limitations for actually enabling us to manage the property and collect rent, but it was a valuable tool for helping us place tenants without having to pay a property manager to do it.

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)?

Much of what I have found says that cashflow is king and that net worth just looks good on paper as cashflow really enables you to live and invest now and banks look more at cashflow and debt/income than they do your net worth (my current debt/income is 14.9%).

@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?