Also: My fear is that, in order to do so, I would have to forgo the VA loan and go with a commercial product.

Yes, mi biggest fear is the I might be emotional about it.

My fear is that an eviction will ultimately need to be done, and the squatter's response is leaving me with a destroyed apartment. 

I've contacted the city and requested they send him a shut-off notice as a scare tactic but specifically told the city NOT to turn off the water for fear of ethical backlash in court from the judge.

I can say that no amount of books alleviated that fear.

@Jon Schwartz, The model is more prevalent than you would think. 

I can afford to buy now and hate to continue throwing money at rent, but I fear it is a bad investment down the line to have a negative cash flow rental property.

https://www.biggerpockets.com/podcast  Hearing from people who are actually doing what you want to do and how they started will give you more confidence and possibly overcome some of the fear. 

I hate to be cliche but to quote Warren Buffett - “We simply attempt to be fearful when others are greedy and to be greedy only when others are fearful.”Time and time again some investment gets hot and the experienced investors sell off to the inexperienced investors somewhere near the top.You don't buy into a hot market you sell into a hot market.It is tough to find cash flow in a hot market.

I fear being screwed over, loosing money, or not succeeding.