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!

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

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.

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%).

I have a Network Attached Server (RAID enabled with 5 hard drives) with 10GB of space. 

I'm new to all of this and would really appreciate someone running through the numbers and theory with me to enable me to better understand whether or not it would make sense for us to house hack now. 

As your renters pay down the mortgages, your net worth increases, enabling you to obtain better financing on your next deal or deals.

I have been listening to a man down in San Antonio that use to have about 15 rental homes and they almost totally broke him when he was able to ask for and get a higher non-refundable deposit,  make the spread between the rent and the debt payment, and often they would make and pay for their own maintenance and improvements, and often they would not take their option and enabled him to do the same thing again.Even though they started out leasing, they tended to treat the home as theirs even though it still belonged to him.