I'm hoping that by registering as a finance company it will also enable me to register as a loan originator, but I have a lot of research to do!

As for my goals, I'd like to supplement and eventually replace my 'day job' income with passive income from real estate. 

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

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".

This might mean sharing profits, but it can also enable you to scale faster.- Consider Short-Term Rentals: Since you're in upstate NY, short-term vacation rentals could be lucrative, especially if you can manage them efficiently.

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.