With that said, there is a de minimis election that allows you to expense any capital expenditures under $2,500 ($5,000 if your business has audited financials). 

I’m in a great spot financially and can’t wait to explore my options and dive in.

If you do this for enough years in a row you should be financially secure and everyone will be jealous how lucky you are! 

The person I sold it to made $40k weeks later doing nothing to the property but listing it on the MLS.All because he had more leverage.He knew I was in a tight situation financially and took advantage of me.He turned me into a motivated seller.

It appears you are focused solely on the financial components of the project without understanding the insurance and liability factors of self-performing the project in the manner in which you propose.

Would not be a wise financial move for most people. 

My attorney advised me and my spouse to setup separate revocable trusts for asset protection but I'm finding that some financial institutions do not allow accounts to be held in title under more than one trust.

I would strongly urge you if you have time to read or listen to Real Estate by the Numbers by Dave Meyer & J Scott because they do a great job of explaining the various numbers and metrics used to make decisions in real estate, it has helped me reframe financial and real estate decisions because I understand the concepts and feel more empowered because of that understanding.The two factors in your decision here are financial and (maybe more importantly) emotional.

Honestly we could afford to go negative monthly without a huge financial burden.

Best of luck on your journey towards financial freedom.