But IF the property in question is in compliance with all code, and provides a safe and secure environment, all problems are timely addressed and corrected, and the property is maintained on a professional level, then the investor who has a large capital investment in the property should be entitled to enforce any contracts providing him with the agreed to cash flow. 

I believe we are in for a very active real estate environment.

I didn't see where you factored in a $3000 mortgage payment (principal & interest only) in today's higher rate environment. 

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

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

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

This is especially in a high rate/high price environment. 

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.

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

Get out of your comfort zone.