.- They actually have the nerve to try and enforce the $100/day penalty for not closing on the agreed upon date even though it had nothing to do with my ability to close.- I finally get pissed enough that I cancel the contract telling them that the only way I will buy it now is with conventional financing and for $5K less than what we had originally agreed upon (my private lender was a family member who was growing increasingly nervous with the situation)

The NAV for my portfolio took a huge hit, but I rode it out, and it ended very well in the end, but it was a nerve racking period.What I would suggest, and what I'm starting to do more of, is to do a stress test of your current deals and portfolio.

Is this just a case of typical nerves surrounding deals early in my RE career or is it no discount no deal?

Really you should engaged a tax CPA/EA who will examine your situation.If your only goal is to be able to buy a primary residence, why don't your parents cash out refi, gift the money to you, preferably under the annual exemption (multiple years if necessary), and you buy a primary? 

I'd suggest getting ahold of the 2019 Marcus and Millichap Report to examine those markets.

I examine everything carefully and fix problems then and there.

I would recommend you examine your investment model and consider replacing it with a better one.

Examine the background qualifications of those in charge/working for the city.

I'm pretty sure it seems so high because I agreed to pay 100% of the closing costs. hmm. i looked back at my primary's fees and they charged:title settlement closing $275; mortgage title policy: $383; title examination:$175; title update $100; title policy: $105. 

I went through the process of examining the 1031 process and rules last year and found that they were generally too inflexible for my needs at the time.