People should do what they are comfortable with and be careful when people use words like "don't", "shouldn't" or "can't" in such a broad context.  

As for leasing, I feel comfortable in that area market to get $14/sf.

Then, compare those returns with the stock market’s historical 8-10% long-term gains to evaluate whether the investment makes sense.Also, consider whether you can comfortably cover the $1,000 monthly shortfall.

Trying to make myself more comfortable with hiring help for setup. 

Get out of your comfort zone.

Since I have damage protection waiver in place I feel more comfortable asking for a smaller deposit.

Of course, YMMV.I would definitely get a good look at the neighborhood around your possbile purchase, and see if you think a nurse would feel comfortable finishing a shift and coming from the hospital to your quadplex alone and in the dark.

I'm having trouble finding a tenant that I feel comfortable leasing the space to.

But now I feel a little stuck because this experience hasn't been good and I'm stuck in a partnership I'm not comfortable with.

You have consider that your average first time home buyer, has no clue how to read an LE, does not even know what fees are for what, and needs that additional assistance for them to feel comfortable purchasing their first property.