Its not highly likely and will set me back 3 years worth of savings.

I then save or scan everything to an encrypted drive and shred any paper. 

I’d say sell that property before something goes wrong then go back to square one, save up for a down payment and ample cash reserves for when something inevitably goes wrong, establish 2 years solid and consistent income, build credit, find a bank to work with and start over again in a better asset class.

In my area of the country, if you can give more value for money than an absentee landlord mailing it in or a faceless management company rapaciously intent on maximizing their profit per unit, you're never going to go broke with rentals in the $700-$1100 range, good economy, bad economy, whatever.

Our savings rate is high but we haven't bought a permanent residence yet.. 1. because our rent is so cheap 2. because we are weighing the options of purchasing a multi-family apartment or something similar 3. because we are a little bit scared of the process.Should we start by purchasing ourselves a home, live in it, fix it up and put it on the rental market or go ahead and start looking for a multi-family unit to purchase with the possibility of living in one of the units & using an FHA 203k loan? 

--Take out the HELOC on the rental and my stockpiled cash and pay off the mortgage on my main home in full and call it a day until the crash comes along when I will have likely saved up more money and have equity in my home, but of an unknown amount.

, do you have any money saved up?

If i was younger, the game plan would be pretty straight forward- go back to school, get a higher paying job, and then save and invest for financial freedom.

However, I feel like the sooner I start, the better, as some of the savings from house hacking (other than creating a rainy day fund for house repairs, of course) can be used to chip away at our student loan burden. 

If you are a certified HVAC person you are saving money there....