I believe you have not had any answers to your question because it is not detailed enough. There are too many variables for someone to provide a comprehensive answer. Why are you closing the corp.? Were you the sole shareholder? Was the capital infusion listed as a loan on the corp. books? Who is authorized to take on debt on behalf of the corp? and many, many more... Furthermore, you are basically asking for free legal advice or, at a minimum, free Accounting advice that would be provided by a CPA. The old adage "You get what you pay for" applies here. Contact a tax attorney and or your CPA.

I consulted with someone in this space. He was extremely knowledgeable and could answer questions quite professionally. It was my recommendation for him to focus on speaking engagements. Many groups are looking for people to come in and speak. If you are experienced in, and knowledgeable about, health insurance and can conduct a good Q&A after your speech it won't take long to carve out a reputation for being an expert in the field. Your phone will start to ring with requests for you to come speak.

This question leads me to believe there are a limited number of people in the company. With that said, and I mean this sincerely; why do you need a title? If you are a key person in an early stage start-up what will the title do for you? Will it pigeon hole you into a specific role or skill set when you are responsible for so much more? One more question; Did you mean the right title for [responsibilities] in a startup? If not, please explain what a "startup title" is?