Also, you should NEVER, EVER be buying a property as-is as a new investor. 

Rather than waiting for a "home run," think about beginning with a more cautious transaction, getting real-world experience, and then progressively growing your portfolio.You can employ house hacking as a strategy since you qualify for a VA loan.

Is there any hope for me to ever recoup my loss? 

Purchase price: $140,000 Cash invested: $50,000 My first ever Multi Family Building that I got at a good deal from my first Mentor into the business.

I am ready to make the big change and feel that I do have the knowledge, yet still maintain the openness to learn and grow; however, I am missing the connections.

The main items in our renovation are:New water main from curb and valveNew electric service and panelAdd bathroom + convert to full bathLVP in 70% of the houseInterior PaintingAdditional bedrooms in basementKitchenette in basementEgress(x2) in basementOur scope of work should create a great living space for us to grow into, but also provide a rental unit that competes (or even exceeds) the area offerings for medium term rentals.

I see a lot of folks mentioning on social media (more Facebook than here) that they wish someone would let them intern for free as a cohost. I think a more ambitious strategy would be to "flood the zone with value" - ...

All paperwork to the tenants should also state that All adults on the premises  have to qualify for the new rents as well as what ever new clauses that you want in there. 

@Nolan Mahoney I’ve got a small but growing number of units (25).

It’s never ever good idea for a Corporation to own assets.