Experience is the best teacher. :) 

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. 

I'm new to real estate and I want to learn how to flip properties and make a profit from them in general. I'm looking for a way to learn directly from someone who's experienced if possible, but I'm not sure where to l...

When it comes to financing, you'd better make sure your teacher, mentor or whatever they might be has the education and experience to back up their instructions and they aren't simply passing on folklore about seller financing!

Lastly, work with someone who has the heart of a teacher, not that of a salesman.

The middle ground, is using a high quality/ full service management company that has a lower cost structure (more tech enabled) and can give you great service for around 15-25%. 

You'd have to check with customer service on compatibility with your particular units but payrange has great bluetooth-enabled apps for laundry payment systems. easy to DIY install with youtube videos. no monthly fees and low upfront hardware acquisition cost.